Bromobenzene [C6H5Br]

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Br

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Conditions & References With carbon dioxide, bromine, Time= 2h, T= 40 °C , p= 187519Torr , Supercritical conditions, Green chemistry Delgado-Abad, Thais; Martnez-Ferrer, Jaime; Reig-Lpez, Javier; Mello, Rossella; Acerete, Rafael; Asensio, Gregorio; Gonzlez-Nez, Mara Elena; RSC Advances; vol. 4; nb. 92; (2014); p. 51016 - 51021 View in Reaxys With lead(II,IV) oxide, trifluoroacetic acid, potassium bromide, T= 20 °C , reagents ratio, Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Rodkin, M. A.; Serguchev, Yu. A.; Davydova, V. G.; Beletskaya, I. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 11; (1987); p. 2424 - 2426; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 11; (1987); p. 2609 - 2611 View in Reaxys With tetrabutylammomium bromide, dihydrogen peroxide, bromine in water, Time= 8h, T= 65 °C , different reagents, Product distribution Dakka, Jihad; Sasson, Yoel; Journal of the Chemical Society, Chemical Communications; nb. 19; (1987); p. 1421 - 1422 View in Reaxys 2.6 Typical procedure for the bromination General procedure: NBS (1.0 mmol) and catalyst 1 (0.1 or 1 mol percent Au based on the substrate) were weighted into a 10 mL sealed vessel, and then DCE (2 mL) and the substrate (1.0 mmol) were added. The reaction was stirred at the required temperature for the specified time. After reaction, the catalyst was removed with a magnet, and the solution was concentrated under reduced pressure and purified by column chromatography.

With N-Bromosuccinimide in 1,2-dichloro-ethane, Time= 11h, T= 80 °C , Sealed tube Li, Bai; Gao, Linfeng; Bian, Fengling; Yu, Wei; Tetrahedron Letters; vol. 54; nb. 9; (2013); p. 1063 - 1066 View in Reaxys With N-Bromosuccinimide, sulfuric acid, trifluoroacetic acid, Time= 2h, T= 25 °C , Bromination Duan, Jianxin; Zhang, Lian Hao; Dolbier Jr., William R.; Synlett; nb. 8; (1999); p. 1245 - 1246 View in Reaxys With sulfuric acid, bromine, mercury(II) oxide in tetrachloromethane, Time= 1h, Heating, other deactivated aromatic rings, Product distribution Khan, Shabbir Afzal; Munawar, M. A.; Siddiq, M.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1799 - 1800 View in Reaxys With sulfuric acid, bromine, mercury(II) oxide in tetrachloromethane, Time= 1h, Heating Khan, Shabbir Afzal; Munawar, M. A.; Siddiq, M.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1799 - 1800 View in Reaxys 3.3. Reactions of 6-BaF2 with arenes 1–4 General procedure: 6-BaF2 (1.92 mmol) was added to corresponding arene 1–4 (5 mL) at room temperature and stirred for 5 h.

The reaction mixture was filtered from solid BaF2, liquid products were analysed by GC–MS and bromoarenes 1a, 2a and 3a were isolated by silica gel flash chromatography, eluent hexane:EtOAc 3:1 (v/v).

With barium fluoride, pyridine*BrF3, Time= 5h, T= 20 °C Sobolev, Vasily I.; Filimonov, Victor D.; Ostvald, Roman V.; Radchenko, Vyacheslav B.; Zherin, Ivan I.; Journal of Fluorine Chemistry; vol. 192; (2016); p. 120 - 123 View in Reaxys With Oxone, sodium bromide in water, Time= 1.5h, T= 20 °C

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Firouzabadi; Iranpoor; Kazemi; Canadian Journal of Chemistry; vol. 87; nb. 12; (2009); p. 1675 - 1681 View in Reaxys With PyHBrCl2, iron(III) chloride in dichloromethane, Time= 1h, T= 20 °C Muathen, Hussni A.; Synthesis; nb. 2; (2002); p. 169 - 171 View in Reaxys With bromine, dinitrogen tetraoxide, pyrographite, ferric nitrate, Time= 2.5h, T= 20 °C Firouzabadi; Iranpoor; Shiri; Tetrahedron Letters; vol. 44; nb. 49; (2003); p. 8781 - 8785 View in Reaxys With ammonium nitrate, N-Bromosuccinimide in acetonitrile, Time= 8h Tanemura, Kiyoshi; Suzuki, Tsuneo; Nishida, Yoko; Satsumabayashi, Koko; Horaguchi, Takaaki; Chemistry Letters; vol.

32; nb. 10; (2003); p. 932 - 933 View in Reaxys With hydrogenchloride, sodium hypochlorite, sodium bromide in water, Time= 8h, T= 29.85 °C , Product distribution, Further Variations: Temperatures, Reagents Sadygov; Alimardanov; Chalabiev; Russian Journal of Organic Chemistry; vol. 41; nb. 11; (2005); p. 1631 - 1636 View in Reaxys With cerium(III) chloride heptahydrate, dihydrogen peroxide, sodium bromide in water, Time= 4.5h, T= 20 °C , regioselective reaction Firouzabadi, Habib; Iranpoor, Nasser; Kazemi, Somayeh; Ghaderi, Arash; Garzan, Atefeh; Advanced Synthesis and Catalysis; vol. 351; nb. 11-12; (2009); p. 1925 - 1932 View in Reaxys 3 :29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70° C. under stirring. A solution of 15.5 ml (35percent) hydrochloric acid (0.15 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 70° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 18.6 g or 81.3percent of clear and colorless liquid bromo benzene having boiling point 154-156° C. With hydrogenchloride, hypobromous acid, sodium dodecyl-sulfate in water, Time= 40h, T= 70 °C , Product distribution / selectivity Patent; Bedekar, Ashutosh Vasant; Ghosh, Kumar Pushpito; Adimurthy, Subbarayyappa; Ramachandraiah, Gadde; US2005/137431; (2005); (A1) English View in Reaxys 3 :EXAMPLE 3; 29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70°C under stirring. A solution of 15.5 ml (35percent) hydrochloric acid (0.15 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 70°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 18.6 g or 81.3percent of clear and colorless liquid bromo benzene having boiling point 154-156°C. With hydrogenchloride, sodium bromate, sodium dodecyl-sulfate, sodium bromide in water, Time= 40h, T= 70 °C , Product distribution / selectivity Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; WO2005/61423; (2005); (A1) English View in Reaxys With thallium (III) oxide, potassium bromide in trifluoroacetic acid, Time= 7h, Ambient temperature

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Gun'kin, I. F.; Russian Journal of General Chemistry; vol. 67; nb. 4; (1997); p. 654 - 655; Zhurnal Obshchei Khimii; vol. 67; nb. 4; (1997); p. 699 - 700 View in Reaxys With methanesulfonic acid, monobromoisocynaurate in diethyl ether, Time= 6h, Heating Okada, Yukihiro; Yokozawa, Masanori; Akiba, Miwa; Oishi, Kazuhiko; O-Kawa, Kyoji; Akeboshi, Tomohiro; Kawamura, Yasuo; Inokuma, Seiichi; Nakamura, Yosuke; Nishimura, Jun; Organic and Biomolecular Chemistry; vol. 1; nb. 14; (2003); p. 2506 - 2511 View in Reaxys With 1,8-diazabicyclo<5.4.0>undec-7-ene hydrobromide perbromide, silver sulfate in sulfuric acid, Time= 0.5h, Ambient temperature, HgCl2 instead Ag2SO4; without Ag2SO4; solvent: DMF or aq. DMF; other temp.; other times; same reaction of other aromatic compounds, Product distribution Muathen, Hussni A.; Journal of Organic Chemistry; vol. 57; nb. 9; (1992); p. 2740 - 2741 View in Reaxys With 1,8-diazabicyclo<5.4.0>undec-7-ene hydrobromide perbromide, silver sulfate in sulfuric acid, Time= 0.5h, Ambient temperature Muathen, Hussni A.; Journal of Organic Chemistry; vol. 57; nb. 9; (1992); p. 2740 - 2741 View in Reaxys With Li2MnO3, bromine, Time= 5h, T= 100 °C , Darkness Nishina, Yuta; Morita, Junya; Ohtani, Bunsho; RSC Advances; vol. 3; nb. 7; (2013); p. 2158 - 2162 View in Reaxys With [2,5-Me2C6H3SO2N(Br)CH2]2 in tetrachloromethane, Time= 1.5h, T= 77 °C , Bromination Ardeshir, Khazaei; Abbas, Shirdarreh; Synthetic Communications; vol. 29; nb. 23; (1999); p. 4079 - 4085 View in Reaxys With pyridine, C36H36N24O12*Br2 in dichloromethane, T= 0 - 75 °C , Reagent/catalyst Reddy; Cavallini; Demets; Silva; New Journal of Chemistry; vol. 38; nb. 6; (2014); p. 2262 - 2264 View in Reaxys 5 :29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 80° C. under stirring. A solution of 22 ml (70percent) perchloric acid (0.15 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 80° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 10.7 g or 53.5percent of clear and colorless liquid bromo benzene having boiling point 154-156° C. With perchloric acid, hypobromous acid, sodium dodecyl-sulfate in water, Time= 40h, T= 80 °C , Product distribution / selectivity Patent; Bedekar, Ashutosh Vasant; Ghosh, Kumar Pushpito; Adimurthy, Subbarayyappa; Ramachandraiah, Gadde; US2005/137431; (2005); (A1) English View in Reaxys 4 :EXAMPLE5; 29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 80°C under stirring. A solution of 22 ml (70percent) perchloric acid (0.15 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 80°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 10.7 g or 53.5percent of clear and colorless liquid bromo benzene having boiling point 154156°C.

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With sodium bromate, perchloric acid, sodium dodecyl-sulfate, sodium bromide in water, Time= 40h, T= 80 °C , Product distribution / selectivity Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; WO2005/61423; (2005); (A1) English View in Reaxys 1; 2; 4 :29.1 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with an water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70° C. under stirring. A solution of 16.4 ml (50percent) sulfuric acid (0.15 mol) was added to the hot reaction mixture over a period for 10 hours. The mixture was stirred for another 30 h at 70° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 20 g or 87.5percent of clear and colorless liquid bromo benzene having boiling point 154-156° C.; 116.4 g of brominating reagent was dissolved in 300 ml water taken in 1000 ml three neck round bottom flask fitted with an water condenser. To it, 5 equivalents (228 ml, 2.92 mol) of benzene per atom of bromine and 0.4 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70° C. under stirring. A solution of 65.6 ml (50percent) sulfuric acid (0.60 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 70° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 82 g or 89.7percent of clear and colorless liquid bromo benzene having boiling point 154-156° C.; 29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 2 equivalents (22.8 ml, 0.292 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70° C. under stirring. A solution of 16.4 ml (50percent) sulfuric acid (0.15 mol) was added to the hot reaction mixture over 8 hours. The mixture was stirred for another 25 h at 80° C. and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether.

The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 11.9 g or 52.3percent of clear and colorless liquid bromo benzene having boiling point 154-156° C. With sulfuric acid, hypobromous acid, sodium dodecyl-sulfate in water, Time= 33 - 40h, T= 70 - 80 °C , Product distribution / selectivity Patent; Bedekar, Ashutosh Vasant; Ghosh, Kumar Pushpito; Adimurthy, Subbarayyappa; Ramachandraiah, Gadde; US2005/137431; (2005); (A1) English View in Reaxys 1-2; 4 :EXAMPLE 1; 29.1 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with an water condenser. To it, 5 equivalents (57 ml, 0.73 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70°C under stirring. A solution of 16.4 ml (50percent) sulfuric acid (0.15 mol) was added to the hot reaction mixture over a period for 10 hours. The mixture was stirred for another 30 h at 70°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 20 g or 87.5percent of clear and colorless liquid bromo benzene having boiling point 154-156°C.; EXAMPLE 2 116.4 g of brominating reagent was dissolved in 300 ml water taken in 1000 ml three neck round bottom flask fitted with an water condenser. To it, 5 equivalents (228 ml, 2.92 mol) of benzene per atom of bromine and 0.4 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70°C under stirring. A solution of 65.6 ml (50percent) sulfuric acid (0.60 mol) was added to the hot reaction mixture over 10 hours. The mixture was stirred for another 30 h at 70°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 82 g or 89.7percent of clear and colorless liquid bromo benzene having boiling point 154-156°C.; EXAMPLE 4 29.10 g of brominating reagent was dissolved in 75 ml water taken in 500 ml three neck round bottom flask fitted with water condenser. To it, 2 equivalents (22.8 ml, 0.292 mol) of benzene per atom of bromine and 0.1 g of sodium lauryl sulfate were added and then the flask was slowly heated to 70°C under stirring. A solution of 16.4 ml (50percent) sulfuric acid (0. 15 mol) was added to the hot reaction mixture over 8 hours. The mixture was stirred for another 25 h at 80°C and then cooled to room temperature. The organic and aqueous layers were separated. The aqueous layer was extracted at least three times with minimum quantity of ether. The extracts were combined with the organic layer, washed successively with water and brine and dried over anhydrous sodium sulfate. Solvent was stripped at reduced pressure to get crude product which was purified by vacuum distillation to give 11.9 g or 52.3percent of clear and colorless liquid bromo benzene having boiling point 154- 156°C.

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With sodium bromate, sulfuric acid, sodium dodecyl-sulfate, sodium bromide in water, Time= 33 - 40h, T= 70 - 80 °C , Product distribution / selectivity Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; WO2005/61423; (2005); (A1) English View in Reaxys With silver(II) sulfate, sulfuric acid, tetra-N-butylammonium tribromide, Time= 0.5h, Ambient temperature Chaudhuri, Mihir K.; Khan, Abu T.; Patel, Bhisma K.; Dey, Deepa; Kharmawophlang, Wancydora; Lakshmiprabha; Mandal, Gagan C.; Tetrahedron Letters; vol. 39; nb. 44; (1998); p. 8163 - 8166 View in Reaxys With sulfuric acid, hydrogen bromide, dihydrogen peroxide in water, Time= 24h, T= 55 °C , Darkness Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Tetrahedron; vol. 65; nb. 22; (2009); p. 4429 - 4439 View in Reaxys With potassium bromate in sulfuric acid, Time= 16h, Ambient temperature Banerjee, Amalendu; Banerjee, Gopal Chandra; Adak, Mohini Mohan; Banerjee, Santa; Samaddar, Haraprasad; Journal of the Indian Chemical Society; vol. 58; (1981); p. 985 - 988 View in Reaxys With manganese triacetate, trifluoroacetic acid, potassium bromide, Time= 15h, Ambient temperature, Co(CH3COO)3, 90percent aq. CF3COOH, 72 h, Product distribution Makhon'kov, D. I.; Cheprakov, A. V.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 609 - 615; Zhurnal Organicheskoi Khimii; vol. 22; nb. 4; (1986); p. 681 - 688 View in Reaxys With bromine, tetramethylammonium bromide in liquid sulphur dioxide, T= -23 °C , var.: in H2O at 25 deg C, NaBr, HClO4, Product distribution, Rate constant Castellonese, Paul; Villa, Pierre; Bulletin de la Societe Chimique de France; vol. 1; nb. 1-2; (1981); p. 42 - 48 View in Reaxys With aluminium trichloride, bromine Leroy; Bulletin de la Societe Chimique de France; vol. <2> 48; (1887); p. 211 View in Reaxys Greene; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 90; (1880); p. 41 View in Reaxys With bromine, beryllium bromide Taboury; Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 328 View in Reaxys With bromine, silver trifluoroacetate Haszeldine; Sharpe; Journal of the Chemical Society; (1952); p. 993,1000 View in Reaxys With bromine, nitric acid Varma; Narayan; ; vol. 4; p. 285; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 489 View in Reaxys With nitrosulfonic acid, bromine, nitric acid Varma; Narayan; ; vol. 4; p. 285; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 489 View in Reaxys With hydrogen bromide, pyrographite, T= 45 °C , Electrolysis Croco; Lowy; ; vol. 50; p. 318; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 421 View in Reaxys

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With bromine Bruner; Chem. Zentralbl.; vol. 71; nb. II; (1900); p. 257 View in Reaxys Couper; Annales de Chimie (Cachan, France); vol. <3> 52; (1858); p. 309; Justus Liebigs Annalen der Chemie; vol. 104; (1857); p. 225 View in Reaxys With bromine, iodine Michaelis; Graeff; Chemische Berichte; vol. 8; (1875); p. 922 View in Reaxys Schramm; Chemische Berichte; vol. 18; (1885); p. 607 View in Reaxys With aluminium amalgam, bromine Cohen; Dakin; Journal of the Chemical Society; vol. 75; (1899); p. 894 View in Reaxys With bromine, zinc(II) chloride Schiaparelli; Gazzetta Chimica Italiana; vol. 11; (1881); p. 69; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1881); p. 539 View in Reaxys With aluminum tri-bromide, bromine Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With thallium chloride, bromine Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, phosphorus trichloride Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, phosphorus tribromide Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, antimony(III) chloride Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, antimony(III) bromide Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With bromine, iron(II) bromide Bruner; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 41; (1902); p. 530 ff View in Reaxys With pyridine, bromine Chross; Cohen; ; p. 335; Chem. Zentralbl.; vol. 79; nb. II; (1908); p. 153 View in Reaxys With potassium bromate, sulfuric acid, bromine

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Krafft; Chemische Berichte; vol. 8; (1875); p. 1045 View in Reaxys With bromosulfur, nitric acid Edinger; Goldberg; Chemische Berichte; vol. 33; (1900); p. 2884 View in Reaxys With bromine, iron Gattermann; View in Reaxys With manganese, bromine, unter Feuchtigkeitsausschluss Ducelliez; Gay; Raynaud; Bulletin de la Societe Chimique de France; vol. <4> 15; (1914); p. 738 View in Reaxys Gay; Ducelliez; Raynaud; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p.

1804; Bulletin de la Societe Chimique de France; vol. <4> 15; (1914); p. 737 View in Reaxys With hypobromous acid Stark; Chemische Berichte; vol. 43; (1910); p. 672 View in Reaxys With bromine, nitric acid Datta; Chatterjee; Journal of the American Chemical Society; vol. 38; (1916); p. 2548 View in Reaxys With sulfuric acid, bromine, nitric acid Varma; Narayan; ; vol. 4; p. 285; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 489 View in Reaxys With bromine, silver perchlorate, magnesium oxide Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys With bromine, nitric acid, silver nitrate, unter Ausschluss von Licht Derbyshire; Waters; Journal of the Chemical Society; (1950); p. 573,576 View in Reaxys With potassium bromate, sulfuric acid in water Harrison, J.J.; Pellegrini, J.P.; Selwitz, C.M.; Journal of Organic Chemistry; vol. 46; nb. 10; (1981); p. 2169 - 2171 View in Reaxys bromination Nakamura, Eiichi; Aoki, Satoshi; Sekiya, Kouichi; Oshino, Hiroji; Kuwajima, Isao; Journal of the American Chemical Society; vol. 109; nb. 26; (1987); p. 8056 - 8066 View in Reaxys With bromine, Time= 6h, T= 25 °C , UV-irradiation, Product distribution, Further Variations: Temperatures Vasilyev, Alexandr V.; Lindeman, Sergey V.; Kochi, Jay K.; New Journal of Chemistry; vol. 26; nb. 5; (2002); p. 582 - 592 View in Reaxys With bromine, Time= 6h, T= -20 °C , Product distribution, Further Variations: Temperatures, reaction times Vasilyev, Alexandr V.; Lindeman, Sergey V.; Kochi, Jay K.; New Journal of Chemistry; vol. 26; nb. 5; (2002); p. 582 - 592 View in Reaxys With zeolite NaY, bromine in dichloromethane, Time= 5h, T= 20 °C , Bromination

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Smith, Keith; El-Hiti, Gamal A.; Hammond, Mark E.W.; Bahzad, Dawoud; Li, Zhaoqiang; Siquet, Christophe; Journal of the Chemical Society, Perkin Transactions 1; nb. 16; (2000); p. 2745 - 2752 View in Reaxys With dihydrogen peroxide, nitric acid, potassium bromide, Ca[V(HIDA)2] in acetonitrile, Time= 6h, T= 20 °C , Bromination Reis; Silva; Frausto da Silva; Pombeiro; Chemical Communications; nb. 19; (2000); p. 1845 - 1846 View in Reaxys With sulfuric acid, dihydrogen peroxide, sodium bromide in water, T= 19.84 °C , Kinetics, Further Variations: Reagents, Temperatures Sadygov; Alimardanov; Chalabiev; Russian Journal of Applied Chemistry; vol. 79; nb. 6; (2006); p. 949 - 956 View in Reaxys 96 :The following compounds presented in Example 96 was prepared in accordance with Scheme 7, by a procedure analogous to that disclosed in Examples 39 and 95, using starting materials with the appropriate substitution.

Patent; REDDY US THERAPEUTICS, INC.; KALLEDA, Srinivas; PADAKANTI, Srinivas; KUMAR SWAMY, Nalivela; YELESWARAPU, Koteswar, Rao; ALEXANDER, Christopher, W.; KHANNA, Ish, Kumar; IQBAL, Javed; PILLARISETTI, Sivaram; PAL, Manojit; BARANGE, Deepak; WO2006/34473; (2006); (A2) English View in Reaxys With gold(III) chloride, N-Bromosuccinimide in dichloromethane, Time= 11h, T= 80 °C , Inert atmosphere Mo, Fanyang; Yan, Jerry Mingtao; Qiu, Di; Li, Fei; Zhang, Yan; Wang, Jianbo; Angewandte Chemie - International Edition; vol. 49; nb. 11; (2010); p. 2028 - 2032 View in Reaxys With dihydrogen peroxide, acetic acid, potassium bromide in water, Time= 6h, T= 60 °C , regioselective reaction Sharma; Sharma, Chetna; Tetrahedron Letters; vol. 51; nb. 33; (2010); p. 4415 - 4418 View in Reaxys With gold(III) chloride, N-Bromosuccinimide in 1,2-dichloro-ethane, Time= 6h, T= 60 °C Qiu, Di; Mo, Fanyang; Zheng, Zhitong; Zhang, Yan; Wang, Jianbo; Organic Letters; vol. 12; nb. 23; (2010); p. 5474 - 5477 View in Reaxys (d) General experimental procedure for oxidative bromination reaction of organic substrates using H2O2 as oxidant and KBr as bromine source at room temperature.

General procedure: Catalytic reaction was carried out in a 50 mL two necked round bottom flask, which charged with 0.05 g of catalyst, substrate (2 mmol) in acetic acid (5 mL) and KBr (2.2 mmol). 30percent H2O2 (2.2 mmol) was then added drop wise to the reaction mixture. The content in the flask was stirred continuously at room temperature. After specified time of the reaction, the catalyst was filtered and the solid was washed with ether. The combined filtrates were washed with saturated sodium bicarbonate solution and then shaken with ether in a separating funnel. The organic extract was dried over anhydrous sodium sulfate.

The products were analysed by Varian 3400 gas chromatograph equipped with a 30 m CP-SIL8CB capillary column and a Flame Ionization Detector. Identity of the products was also confirmed by using an Agilent GC-MS. With dihydrogen peroxide, acetic acid, potassium bromide in water, Time= 6h, T= 20 °C Islam; Roy, Anupam Singha; Mondal, Paramita; Tuhina, Kazi; Mobarak, Manir; Mondal, John; Tetrahedron Letters; vol.

53; nb. 2; (2012); p. 127 - 131 View in Reaxys With sulfuric acid, dihydrogen peroxide, potassium bromide in water, Time= 6h, T= 20 °C Islam, Sk. Manirul; Roy, Anupam Singha; Mondal, Paramita; Salam, Noor; Journal of Molecular Catalysis A: Chemical; vol. 358; (2012); p. 38 - 48 View in Reaxys With N-Bromosuccinimide, Time= 16h, T= 80 °C Zhang, Rui; Huang, Lei; Zhang, Yanfang; Chen, Xiaorong; Xing, Weihong; Huang, Jun; Catalysis Letters; vol. 142; nb. 3; (2012); p. 378 - 383 View in Reaxys

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With N-Bromosuccinimide, 1,1,2,2-tetrafluoroethanesulfonic acid, Time= 4h, T= 20 °C Prakash, G. K. Surya; Mathew, Thomas; Panja, Chiradeep; Kulkarni, Aditya; Olah, George A.; Harmer, Mark A.; Advanced Synthesis and Catalysis; vol. 354; nb. 11-12; (2012); p. 2163 - 2171 View in Reaxys With bromine, Time= 1.5h, T= 40 °C , Darkness, Inert atmosphere, Green chemistry Nishina, Yuta; Takami, Keishi; Green Chemistry; vol. 14; nb. 9; (2012); p. 2380 - 2383 View in Reaxys With dihydrogen peroxide in acetic acid, Time= 5h, T= 20 °C Islam, Sk. M.; Roy, Anupam Singha; Mondal, Paramita; Salam, Noor; Paul, Sumantra; Catalysis Letters; vol. 143; nb. 2; (2013); p. 225 - 233 View in Reaxys With bromine in hexane, Time= 0.0833333h, T= 25 °C , Darkness Ross, Joanne C.; Clark, James H.; Macquarrie, Duncan J.; Barlow, Simon J.; Bastock, Tony W.; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 245 - 249 View in Reaxys Reaction Steps: 2 1: hydrogenchloride; 3-chloro-benzenecarboperoxoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With hydrogenchloride, 3-chloro-benzenecarboperoxoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys Reaction Steps: 2 1: tetrafluoroboric acid; 3-chloro-benzenecarboperoxoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With tetrafluoroboric acid, 3-chloro-benzenecarboperoxoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys Reaction Steps: 2 1: hydrogen bromide; 3-chloro-benzenecarboperoxoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With hydrogen bromide, 3-chloro-benzenecarboperoxoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys Reaction Steps: 2 1: 3-chloro-benzenecarboperoxoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With 3-chloro-benzenecarboperoxoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys Reaction Steps: 2 1: 3-chloro-benzenecarboperoxoic acid 2: copper(I) bromide / acetonitrile / 2 h / 80 °C With 3-chloro-benzenecarboperoxoic acid, copper(I) bromide in acetonitrile Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys With bromine

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Parsons, Brendon A.; Smith, Olivia Lin; Chae, Myeong; Dragojlovic, Veljko; Beilstein Journal of Organic Chemistry; vol.

11; (2015); p. 980 - 993 View in Reaxys With bromine in dichloromethane-d2, T= 24.84 °C , Kinetics, Concentration, Temperature Shernyukov, Andrey V.; Genaev, Alexander M.; Salnikov, George E.; Rzepa, Henry S.; Shubin, Vyacheslav G.; Journal of Computational Chemistry; vol. 37; nb. 2; (2016); p. 210 - 225 View in Reaxys With N-Bromosuccinimide, acetic acid in 1,2-dichloro-ethane, Time= 0.5h, T= 80 °C , Temperature Losch; Kolb; Astafan; Daou; Pinard; Pale; Louis; Green Chemistry; vol. 18; nb. 17; (2016); p. 4714 - 4724 View in Reaxys With N-Bromosuccinimide, CH6B11Br6 (1-)*Li(1+), Time= 24h, T= 100 °C , Schlenk technique, Glovebox, Darkness, Reagent/ catalyst Kitazawa, Yu; Takita, Ryo; Yoshida, Kengo; Muranaka, Atsuya; Matsubara, Seijiro; Uchiyama, Masanobu; Journal of Organic Chemistry; vol. 82; nb. 4; (2017); p. 1931 - 1935 View in Reaxys With bromine, iron in dichloromethane, Time= 2.33333h, Inert atmosphere Guan, Liangyu; Holl, Maxwell Gargiulo; Pitts, Cody Ross; Struble, Mark D.; Siegler, Maxime A.; Lectka, Thomas; Journal of the American Chemical Society; vol. 139; nb. 42; (2017); p. 14913 - 14916 View in Reaxys With dihydrogen peroxide, potassium bromide in water, acetic acid, Time= 6h, T= 20 °C , Green chemistry, Catalytic behavior Khatun, Resmin; Biswas, Surajit; Ghosh, Swarbhanu; Islam, Sk. Manirul; Journal of Organometallic Chemistry; vol. 858; (2018); p. 37 - 46 View in Reaxys

Br

Br I

Rx-ID: 1981474 View in Reaxys 2/513 Yield

Conditions & References With Triethoxysilane, C20H24N4Ni, sodium t-butanolate in toluene, Time= 8h, T= 80 °C , Inert atmosphere, Schlenk technique, Kumada Cross-Coupling Wang, Zijing; Li, Xiaoyan; Sun, Hongjian; Fuhr, Olaf; Fenske, Dieter; Organometallics; vol. 37; nb. 4; (2018); p. 539 - 544 View in Reaxys With hydrogen cation, copper, 1) THF, -78 deg C, 10 min, Yield given. Multistep reaction Ebert, Greg W.; Pfennig, Deborah R.; Suchan, Scott D.; Donovan Jr., Thomas A.; Tetrahedron Letters; vol. 34; nb. 14; (1993); p. 2279 - 2282 View in Reaxys With hydrogenchloride, CuI*P(Et)3, naphthalen-1-yl-lithium, 1.) THF, -78 deg C, 10 min, Yield given. Multistep reaction Ebert, Greg W.; Pfennig, Deborah R.; Suchan, Scott D.; Donovan, Thomas A.; Aouad, Emmanuel; et al.; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2361 - 2364 View in Reaxys With tetrabutylammomium bromide, palladium diacetate, potassium hydroxide, 2′-(diphenylphosphino)-N,N′-dimethyl-(1,1′-biphenyl)-2-amine in methanol, water, T= 120 °C , Microwave irradiation Sandtorv, Alexander H.; Bjørsvik, Hans-René; ChemCatChem; vol. 7; nb. 14; (2015); p. 2196 - 2205 View in Reaxys

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Si

Br

Br

Rx-ID: 47525182 View in Reaxys 3/513 Yield

Conditions & References With potassium trimethylsilonate in dimethyl sulfoxide, Time= 6h, T= 70 °C , Sealed tube, Schlenk technique Yao, Wubing; Li, Rongrong; Jiang, Huajiang; Han, Deman; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 2250 2255 View in Reaxys HO

Br

Br

B HO

Br

Br

Rx-ID: 47840890 View in Reaxys 4/513 Yield

Conditions & References Study of the catalytic activity of compounds 1a-f and 4 in the Suzuki-Miyaura reaction (general procedure).

General procedure: The corresponding base (0.7 mmol) (see Tables 2 and 3) was mixed with a solution of aryl halide 3a-l (0.25 mmol), phenylboronic acid (42 mg, 0.35 mmol), and tetrabutylammonium bromide (81 mg, 0.25 mmol) in propan-2-ol (1 mL) in a 7 mL glass vial with a screw cap equipped with a magnetic stirrer. A solution (10 μL) of the corresponding catalyst in DMF was added, and the mixture was purged with argon and stirred at 80 °C for 2-5 h (see Tables 2 and 3). Then the reaction mixture was cooled, and naphthalene (16 mg, 0.125 mmol) as an internal GCMS standard was added. An aliquot (1 μL) of the reaction mixture was dissolved in acetonitrile (1 mL), and the sample was analyzed by GCMS. With (2,4-dibenzyl-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)(dibromo)(pyridine)palladium, tetrabutylammomium bromide in N,N-dimethyl-formamide, isopropyl alcohol, Time= 2h, T= 80 °C , Inert atmosphere, Suzuki-Miyaura Coupling, Reagent/catalyst Chernenko, A. Yu.; Astakhov; Pasyukov; Dorovatovskii; Zubavichus, Ya. V.; Khrustalev; Chernyshev; Russian Chemical Bulletin; vol. 67; nb. 1; (2018); p. 79 - 84; Izv. Akad. Nauk, Ser. Khim.; nb. 1; (2018); p. 79 - 84,6 View in Reaxys

H 2N

Br

Rx-ID: 712765 View in Reaxys 5/513 Yield

Conditions & References With trimethylsilyl bromide, N-benzyl-N,N,N-triethylammonium chloride, sodium nitrite in tetrachloromethane, 1.) 0 deg C, 1.5 h, 2.) r.t., 10 h Lee, Jong Gun; Cha, Hee Tae; Tetrahedron Letters; vol. 33; nb. 22; (1992); p. 3167 - 3168 View in Reaxys Stage 1: With Bromotrichloromethane, sodium nitrite in dichloromethane, water, Time= 0.0833333h, T= 23 °C Stage 2: With acetic acid in dichloromethane, water, Time= 1h, T= 23 °C Leas, Derek A.; Dong, Yuxiang; Vennerstrom, Jonathan L.; Stack, Douglas E.; Organic Letters; vol. 19; nb. 10; (2017); p.

2518 - 2521 View in Reaxys With copper(I) bromide, hydrogen bromide, sodium nitrite, multistep reaction; diazotization and Sandmeyer reaction in polyethylene glycol-CH2Cl2; 0 deg C to r.t.

Suzuki, Nobutaka; Kaneko, Yoshihiro; Nomoto, Tateo; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 22; (1984); p. 1523 - 1524 View in Reaxys

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Reaktion ueber mehrere Stufen Sandmeyer; Chemische Berichte; vol. 17; (1884); p. 2651 View in Reaxys With tert.-butylnitrite, copper(ll) bromide in acetonitrile Doyle,M.P. et al.; Journal of Organic Chemistry; vol. 42; (1977); p. 2426 - 2431 View in Reaxys With copper(I) bromide, hydrogen bromide, sodium nitrite, 1.) water, poly(ethylene glycol), CH2Cl2, 0 deg C; 2.) poly(ethylene glycol), CH2Cl2, from 0 deg C to RT, Yield given. Multistep reaction Suzuki, Nobutaka; Azuma, Terukazu; Kaneko, Yoshihiro; Izawa, Yasuji; Tomioka, Hideo; Nomoto, Tateo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 645 - 648 View in Reaxys With tert-Butyl thionitrate, copper(ll) bromide in acetonitrile, Time= 0.0333333h, T= 25 °C Oae, Shigeru; Shinhama, Koichi; Kim, Yong Hae; Bulletin of the Chemical Society of Japan; vol. 53; nb. 4; (1980); p. 1065 1069 View in Reaxys

I

Br

Br

Rx-ID: 2011203 View in Reaxys 6/513 Yield

Conditions & References With potassium carbonate, iron pentacarbonyl in methanol, Time= 48h, T= 60 °C , p= 760Torr Brunet, Jean-Jacques; Taillefer, Marc; Journal of Organometallic Chemistry; vol. 348; (1988); p. C5 - C8 View in Reaxys With butyl magnesium bromide, zirconocene dichloride in tetrahydrofuran, Time= 1h, Ambient temperature Hara, Ryuichiro; Sun, Wen-Hua; Nishihara, Yasushi; Takahashi, Tamotsu; Chemistry Letters; nb. 12; (1997); p. 1251 1252 View in Reaxys With tris-(trimethylsilyl)silane in acetonitrile, Time= 24h, Schlenk technique, Inert atmosphere, Irradiation Jiang, Hao; Bak, Jesper R.; Lopez-Delgado, Francisco Javier; Jorgensen, Karl Anker; Green Chemistry; vol. 15; nb. 12; (2013); p. 3355 - 3359 View in Reaxys Generalmethod for the hydrodehalogenation General procedure: Aryl iodide or bromides (5.0 mmol),paraformaldehyde (5.0 mmol), Pd(OAc)2 (0.0005 mmol) (for aryliodides) or Pd(PPh3)4 (0.05 mmol) (for aryl bromides) andCs2CO3 (7.0 mmol) were reacted in DMSO at 80 oCfor 12 h. The reaction mixture was poured into H2O, and extractedwith Et2O. The internal standard (dodecane) was added to theresulting mixture, and the conversion of aryl iodide and the yield of thehydrodehalogenated product were calculated.

With formaldehyd, palladium diacetate, caesium carbonate in dimethyl sulfoxide, Time= 12h, T= 80 °C Pyo, Ayoung; Kim, Sudeok; Kumar, Manian Rajesh; Byeun, Aleum; Eom, Min Sik; Han, Min Su; Lee, Sunwoo; Tetrahedron Letters; vol. 54; nb. 38; (2013); p. 5207 - 5210 View in Reaxys With hydrogenchloride, CuI*P(Et)3, naphthalen-1-yl-lithium, 1.) THF, 25 deg C, 30 min, Yield given. Multistep reaction Ebert, Greg W.; Pfennig, Deborah R.; Suchan, Scott D.; Donovan, Thomas A.; Aouad, Emmanuel; et al.; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2361 - 2364 View in Reaxys With Amberlite IRA-400, borohydride form, copper(II) sulfate in methanol, Time= 1h, T= 20 °C , Reduction

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Sim, Tae Bo; Yoon, Nung Min; Bulletin of the Chemical Society of Japan; vol. 70; nb. 5; (1997); p. 1101 - 1107 View in Reaxys With potassium fluoride, polymethylhydrosiloxane, bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran, Time= 26h, T= 20 °C Maleczka Jr., Robert E.; Rahaim Jr., Ronald J.; Teixeira, Robson R.; Tetrahedron Letters; vol. 43; nb. 39; (2002); p. 7087 7090 View in Reaxys With triethylamine, Lumogen F Orange 240 in N,N-dimethyl-formamide, Time= 48h, T= 40 °C , Irradiation, chemoselective reaction Ghosh, Indrajit; Ghosh, Tamal; Bardagi, Javier I.; König, Burkhard; Science; vol. 346; nb. 6210; (2014); p. 725 - 728 View in Reaxys 4.2 General procedure for the dehalogenation of aryl iodides General procedure: A Schlenk tube was charged with aryl iodides (0.5mmol), phen (18mg, 0.1mmol) and t-BuOK (112mg, 1.0mmol) under an atmosphere of nitrogen at room temperature, and then THF (4.0mL) was added. The resulting mixture was stirred at 70°C for 24h. After cooling to room temperature, the reaction mixture was quenched and extracted with ethyl ether (10mL×3). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure, and then purified by silica gel chromatograph to yield the desired dehalogenation product.

With tetrahydrofuran, 1,10-Phenanthroline, potassium tert-butylate, Time= 24h, T= 70 °C , Schlenk technique, Inert atmosphere, chemoselective reaction Liu, Wei; Hou, Fanyi; Tetrahedron; vol. 73; nb. 7; (2017); p. 931 - 937 View in Reaxys

Br

NH 2

Br

Rx-ID: 3752706 View in Reaxys 7/513 Yield

Conditions & References Stage 1: With tetrafluoroboric acid, acetic acid, isopentyl nitrite in water, Time= 0.0833333h, T= 18 °C Stage 2: With eosin Y disodium salt in N,N-dimethyl-formamide, Time= 6h, T= 18 °C , Inert atmosphere, UV-irradiation, Schlenk technique, Concentration, Reagent/catalyst, Solvent Majek, Michal; Von Wangelin, Axel Jacobi; Chemical Communications; vol. 49; nb. 48; (2013); p. 5507 - 5509 View in Reaxys With formamide, triethylamine, trifluoroacetic acid, sodium nitrite, 1.) formamide/water, r.t.; 2.) water, r.t., Yield given. Multistep reaction Threadgill, Michael D.; Gledhill, Adrian P.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1986); p. 873 - 876 View in Reaxys Stage 1: With Nitrogen dioxide in acetonitrile, T= -20 °C , Diazotization Stage 2: With calcium bis(hypophosphite), Fe2SO4*7H2O in methanol, acetonitrile, T= 20 °C , Dediazonation Mitsuhashi, Hirokazu; Kawakami, Takehiko; Suzuki, Hitomi; Tetrahedron Letters; vol. 41; nb. 29; (2000); p. 5567 - 5569 View in Reaxys Stage 1: With tetrafluoroboric acid, acetic acid, isopentyl nitrite in water, Time= 0.0833333h, T= 20 °C Stage 2: With eosin B disodium salt in N,N-dimethyl-formamide, Time= 0.5h, T= 18 °C , Inert atmosphere, Irradiation Majek, Michal; Filace, Fabiana; Von Wangelin, Axel Jacobi; Chemistry - A European Journal; vol. 21; nb. 12; (2015); p.

4518 - 4522 View in Reaxys With tetrahydrofuran, tert.-butylnitrite, salicylic acid, Time= 3h, T= 20 °C , Schlenk technique, Inert atmosphere

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Felipe-Blanco, Diego; Alonso, Francisco; Gonzalez-Gomez, Jose C.; Advanced Synthesis and Catalysis; vol. 359; nb. 16; (2017); p. 2857 - 2863 View in Reaxys

Br Br

Br

Rx-ID: 3960133 View in Reaxys 8/513 Yield

Conditions & References With sodium bis(2-methoxyethoxy)aluminium dihydride in toluene, T= 70 °C , Rate constant Vcelak, Jaroslav; Friesova, Anna; Rericha, Roman; Hetflejs, Jiri; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 6; (1994); p. 1368 - 1383 View in Reaxys 2.3. General photocatalytic reaction procedures General procedure: Photocatalytic reduction reactions were carried out using a LZ4-X Luzchem Photoreactor with eightfluorescent bulbs generatingapproximately 70 W/m-2 from 400 to 440 nm. Reaction solutionswere added to disposable borasillicate test tubes and sealed withrubber septa. Prior to photolysis, all of the samples were spargedwith argon for at least 30 min and sonicated to break up theheterogeneous photocatalyst powder. During the photoreaction,the samples were stirred and the temperature held constant at 25–30 °C. The product analysis was performed using an Agilent 1200Series HPLCfitted with a UV–vis diode array detector.

With formic acid, titanium(IV) oxide, triethylamine in acetonitrile, Time= 4h, T= 25 - 30 °C , Sealed tube, Photolysis Petroff II, John T.; Nguyen, Anh H.; Porter, Alex J.; Morales, Fraisher D.; Kennedy, Michael P.; Weinstein, David; Nazer, Hossam El; McCulla, Ryan D.; Journal of Photochemistry and Photobiology A: Chemistry; vol. 335; (2017); p. 149 - 154 View in Reaxys With ZnSe/CdS core/shell QDs, N-ethyl-N,N-diisopropylamine in hexane, Time= 48h, T= 25 °C , Irradiation, Inert atmosphere Pal, Anuushka; Ghosh, Indrajit; Sapra, Sameer; König, Burkhard; Chemistry of Materials; vol. 29; nb. 12; (2017); p. 5225 - 5231 View in Reaxys

Br

I

Br

Rx-ID: 4158886 View in Reaxys 9/513 Yield

Conditions & References With hydrogenchloride, CuI*P(Et)3, naphthalen-1-yl-lithium, 1.) THF, 25 deg C, 60 min, Yield given. Multistep reaction Ebert, Greg W.; Pfennig, Deborah R.; Suchan, Scott D.; Donovan, Thomas A.; Aouad, Emmanuel; et al.; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2361 - 2364 View in Reaxys 4.2 General procedure for the dehalogenation of aryl iodides General procedure: A Schlenk tube was charged with aryl iodides (0.5mmol), phen (18mg, 0.1mmol) and t-BuOK (112mg, 1.0mmol) under an atmosphere of nitrogen at room temperature, and then THF (4.0mL) was added. The resulting mixture was stirred at 70°C for 24h. After cooling to room temperature, the reaction mixture was quenched and extracted with ethyl ether (10mL×3). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure, and then purified by silica gel chromatograph to yield the desired dehalogenation product.

With tetrahydrofuran, 1,10-Phenanthroline, potassium tert-butylate, Time= 24h, T= 70 °C , Schlenk technique, Inert atmosphere, chemoselective reaction Liu, Wei; Hou, Fanyi; Tetrahedron; vol. 73; nb. 7; (2017); p. 931 - 937 View in Reaxys

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HO B

Br

Br

HO

Rx-ID: 39871999 View in Reaxys 10/513 Yield

Conditions & References With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I), water in toluene, Time= 1h, T= 90 °C , Microwave irradiation, Green chemistry Barker, Graeme; Webster, Stacey; Johnson, David G.; Curley, Rachel; Andrews, Matthew; Young, Paul C.; MacGregor, Stuart A.; Lee, Ai-Lan; Journal of Organic Chemistry; vol. 80; nb. 20; (2015); p. 9807 - 9816 View in Reaxys With silver nitrate, triethylamine in ethanol, water, Time= 0.25h, T= 80 °C Liu, Chun; Li, Xinmin; Wu, Yonghua; RSC Advances; vol. 5; nb. 20; (2015); p. 15354 - 15358 View in Reaxys With acetic acid, Time= 5h, T= 110 °C , Green chemistry Zhang, Guoqing; Li, Yang; Liu, Jianhui; RSC Advances; vol. 7; nb. 56; (2017); p. 34959 - 34962 View in Reaxys 5 : Example 5 p-Bromoboric acid (1 mmol),Potassium methoxide (0.05 mmol), 2 mL of methanol or ethanol were successively added into a 10 mL sealed tube, heated and stirred in a 120 ° C. oil bath for 12 hours,The reaction was completed and the exact yield of the product was determined by GC by adding an equivalent of mesitylene to the crude product as an internal standard.According to GC, when using methanol or ethanol as the reaction solvent, the yields were 81percent and 78percent, respectively.

With potassium methanolate in methanol, Time= 12h, T= 120 °C , Sealed tube, Green chemistry, Catalytic behavior, Solvent Patent; Taizhou University; Yao Wubing; (7 pag.); CN107188773; (2017); (A) Chinese View in Reaxys

H 2N Br

Br

Rx-ID: 40509758 View in Reaxys 11/513 Yield

Conditions & References Stage 1: With tetrafluoroboric acid, acetic acid, isopentyl nitrite in water, Time= 0.0833333h, T= 20 °C Stage 2: With eosin B disodium salt in N,N-dimethyl-formamide, Time= 0.5h, T= 18 °C , Inert atmosphere, Irradiation Majek, Michal; Filace, Fabiana; Von Wangelin, Axel Jacobi; Chemistry - A European Journal; vol. 21; nb. 12; (2015); p.

4518 - 4522 View in Reaxys With tetrahydrofuran, tert.-butylnitrite, salicylic acid, Time= 3h, T= 20 °C , Schlenk technique, Inert atmosphere Felipe-Blanco, Diego; Alonso, Francisco; Gonzalez-Gomez, Jose C.; Advanced Synthesis and Catalysis; vol. 359; nb. 16; (2017); p. 2857 - 2863 View in Reaxys Br

HO Br

B HO

Rx-ID: 44171125 View in Reaxys 12/513 Yield

Conditions & References Reaction Steps: 2 1: toluene / Dean-Stark; Inert atmosphere 2: cesium acetate; triethylamine; diethyl malonate; copper dichloride / 1,2-dichloro-ethane / 48 h / 20 °C / Inert atmosphere

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With cesium acetate, triethylamine, diethyl malonate, copper dichloride in 1,2-dichloro-ethane, toluene Moon, Patrick J.; Halperin, Heather M.; Lundgren, Rylan J.; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1894 - 1898; Angew. Chem.; vol. 128; nb. 5; (2016); p. 1926 - 1930,5 View in Reaxys With acetic acid, Time= 5h, T= 110 °C , Green chemistry Zhang, Guoqing; Li, Yang; Liu, Jianhui; RSC Advances; vol. 7; nb. 56; (2017); p. 34959 - 34962 View in Reaxys O Br

Cl

HO

Rx-ID: 45815761 View in Reaxys 13/513 Yield 87 %

Conditions & References 9 : Chlorodecarboxylation of benzoic acid. Optimization of the reaction conditions. chloroisocyanurate/brominating agent General procedure: Round bottom flask equipped with Dimroth condenser (chilled to -10 °C) was charged with benzoic acid (0.8 mmol), chloroisocyanurate, brominating agent and solvent (4 mL). The mixture was magnetically stirred and heated in an oil bath under fluorescent room light irradiation (FL). The yields of chloro- and bromobenzenes were determined by gas chromatography (GC) using l-chloro-2-fluorobenzene as internal standard. The results are presented in Table 6 With trichloroisocyanuric acid, bromine in tetrachloromethane, Time= 4h, T= -10 - 100 °C , Photolysis Patent; TECHNION RESEARCH and DEVELOPMENT FOUNDATION LIMITED; GANDELMAN, Mark; NISNEVICH, Gennady A.; KULBITSKI, Kseniya; ARTARYAN, Alexander; (65 pag.); WO2017/60906; (2017); (A1) English View in Reaxys

Br

Br

HO

Rx-ID: 46312113 View in Reaxys 14/513 Yield

Conditions & References With [(′(4)-cycloocta-1,5-diene)RhCl2], tris-(o-tolyl)phosphine, Time= 12h, T= 177 °C , Schlenk technique, Inert atmosphere Mazziotta, Andrea; Madsen, Robert; European Journal of Organic Chemistry; vol. 2017; nb. 36; (2017); p. 5417 - 5420 View in Reaxys

O

O

O N

O

N

N

Br

N (v2)

F

Rx-ID: 46489723 View in Reaxys 15/513 Yield

Conditions & References Reaction Steps: 3 1: benzene-d6 / 48 h / 20 °C 2: 1 h / Inert atmosphere; Photolysis 3: benzene-d6 / 48 h / 20 °C in benzene-d6, 2: |Buchner Ring Enlargement Perera, Tharushi A.; Reinheimer, Eric W.; Hudnall, Todd W.; Journal of the American Chemical Society; vol. 139; nb. 41; (2017); p. 14807 - 14814 View in Reaxys

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O

O

N

N Br

Cl

Rx-ID: 46489734 View in Reaxys 16/513 Yield

Conditions & References Reaction Steps: 3 1: benzene-d6 / 48 h / 20 °C 2: 1 h / Inert atmosphere; Photolysis 3: benzene-d6 / 48 h / 20 °C in benzene-d6, 2: |Buchner Ring Enlargement Perera, Tharushi A.; Reinheimer, Eric W.; Hudnall, Todd W.; Journal of the American Chemical Society; vol. 139; nb. 41; (2017); p. 14807 - 14814 View in Reaxys

O

O

O N

O

N

N

Br

N (v2)

Br

Rx-ID: 46489744 View in Reaxys 17/513 Yield

Conditions & References in benzene-d6, Time= 48h, T= 20 °C Perera, Tharushi A.; Reinheimer, Eric W.; Hudnall, Todd W.; Journal of the American Chemical Society; vol. 139; nb. 41; (2017); p. 14807 - 14814 View in Reaxys

O

O

N

N

Br

Rx-ID: 46489772 View in Reaxys 18/513 Yield

Conditions & References Reaction Steps: 3 1: benzene-d6 / 2 h / 60 °C 2: 1 h / Inert atmosphere; Photolysis 3: benzene-d6 / 48 h / 20 °C in benzene-d6, 2: |Buchner Ring Enlargement Perera, Tharushi A.; Reinheimer, Eric W.; Hudnall, Todd W.; Journal of the American Chemical Society; vol. 139; nb. 41; (2017); p. 14807 - 14814 View in Reaxys

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-1 F (v4)

F

B FF

Br N

+

N

Rx-ID: 5326846 View in Reaxys 19/513 Yield

Conditions & References With copper diacetate, potassium bromide in water, acetone, Substitution Grishchuk; Gorbovoi; Zagrichuk; Ganushchak; Kudrik; Russian Journal of General Chemistry; vol. 69; nb. 8; (1999); p.

1299 - 1303 View in Reaxys With (triphenylphosphine)gold(I) chloride, sodium bromide in acetonitrile, Time= 5h, T= 50 °C , Sandmeyer Reaction Peng, Haihui; Cai, Rong; Xu, Chang; Chen, Hao; Shi, Xiaodong; Chemical Science; vol. 7; nb. 9; (2016); p. 6190 - 6196 View in Reaxys

HN

Br

Br

H 2N

Rx-ID: 42783223 View in Reaxys 20/513 Yield

Conditions & References With potassium trimethylsilonate in d7-N,N-dimethylformamide, Time= 9h, T= 20 °C Kubovičová, Lenka; Bürglová, Kristýna; Hlaváč, Jan; Organic and Biomolecular Chemistry; vol. 14; nb. 21; (2016); p. 4824 - 4828 View in Reaxys

Br Br

Br

Br

F Br

Br

Rx-ID: 43872307 View in Reaxys 21/513 Yield 12 %Chromat., 17 %Chromat., 8 %Chromat., 34 %Chromat.

Conditions & References 3.1. Reactions of TFBs with arenes 1–4 General procedure: TFBs were synthesized using previously described methods [7–9] directly before use. Corresponding arene (4 mmol) was dissolved in Freon R 113 (4.1 mL), and cooled to -25°C. The corresponding TFB (2 mmol) was slowly added to the arene solution with vigorous stirring and the cooling bath was removed. The reaction mass was stirred at 45°C for 5 h. After reaction completion the reaction mass was treated by H2O and filtered to remove the metal fluoride precipitate. The liquid phase was treated by 10percent aqueous NaNO2 in order to remove traces of bromine and with 30percent aqueous CaCl2 to remove the F- anion. Freon R 113 was evaporated from the organic phase and the obtained product purified by silica gel flash chromatography, eluent hexane:EtOAc. With 2BrF4H(1-)*Ba(2+) in 1,1,2-Trichloro-1,2,2-trifluoroethane, Time= 5h, T= 45 °C Sobolev, Vasily I.; Filimonov, Victor D.; Ostvald, Roman V.; Radchenko, Vyacheslav B.; Zherin, Ivan I.; Journal of Fluorine Chemistry; vol. 192; (2016); p. 120 - 123 View in Reaxys

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Br

O Br

B

B

O

O

O

O

B O

O

Br

O

Br

O Br

O O

Rx-ID: 44171113 View in Reaxys 22/513 Yield

Conditions & References With copper diacetate, triethylamine in toluene, Time= 66h, T= 30 °C , Inert atmosphere, Sealed tube, Reagent/catalyst Moon, Patrick J.; Halperin, Heather M.; Lundgren, Rylan J.; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1894 - 1898; Angew. Chem.; vol. 128; nb. 5; (2016); p. 1926 - 1930,5 View in Reaxys Br

O Br

B

B

O

Br

O B

Br

Rx-ID: 44171124 View in Reaxys 23/513 Yield

Conditions & References With cesium acetate, triethylamine, diethyl malonate, copper dichloride in 1,2-dichloro-ethane, Time= 48h, T= 20 °C , Inert atmosphere, Reagent/catalyst Moon, Patrick J.; Halperin, Heather M.; Lundgren, Rylan J.; Angewandte Chemie - International Edition; vol. 55; nb. 5; (2016); p. 1894 - 1898; Angew. Chem.; vol. 128; nb. 5; (2016); p. 1926 - 1930,5 View in Reaxys

Br

Br

Br

Br

H

Rx-ID: 44281099 View in Reaxys 24/513 Yield 477.2 kg

Conditions & References 1 :The reactor was charged with 468 Kg of benzene in a 1000 L stirred vessel equipped with a 4-m enamel packed tower and a dephlegmator. The catalyst 0.6 Kg anhydrous ferric chloride was heated to 75 °C. 480 Kg of bromine was introduced into the bromine drop tank. Open the top of the sub-condensers into the water, the synthesis reactor temperature to 75 °C or so, to keep the tower back to the state, open the reactor bromine drip bottom of the valve drops bromine, dropping time 8 hr. The reaction temperature was gradually increased during the process. The system maintained the micro-refluxing state in the column and maintained the 95-105 °C reaction for 2 hours. The tail gas is absorbed by three cascade falling film water, and 240kg water is added to the single stage, and the absorption temperature is 15 ~ 60 °C. After the synthesis of liquid benzene, refined to bromine

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benzene 425.6Kg, content of 99.3percent. Exhaust gas absorption of a recovery of hydrogen bromide 477.2Kg, content of 48.57percent, the appearance of a colorless transparent liquid, free bromine content 23PPM. With iron(III) chloride, Time= 10h, T= 75 - 105 °C , Industrial scale, Reagent/catalyst, Temperature Patent; Jiangsu Youjia Chemical Co., Ltd; Jiangsu Yangnong Chemical Co., Ltd; XU, HAIPENG; WANG, ZHENFENG; PENG, DA; WU, CHUNZHONG; DING, JIANJIAN; YIN, WEIDONG; (5 pag.); CN102964209; (2016); (B) Chinese View in Reaxys -1 F (v4)

F

B FF

Br N+

Br

N

Rx-ID: 2327217 View in Reaxys 25/513 Yield

Conditions & References With N-benzyl-1,4-dihydronicotinamide in methanol, Time= 0.166667h, Ambient temperature, add of oxygen or N-t-butyl-′phenylnitrone, Mechanism Yasui, Shinro; Nakamura, Kaoru; Ohno, Atsuyoshi; Tetrahedron Letters; vol. 24; nb. 32; (1983); p. 3331 - 3334 View in Reaxys With pyrene in acetonitrile, Irradiation, CIDNP effects of the photochemical dediazonation; reaction in the absence of pyrene in dioxane Becker, Heinz G. O.; Pfeifer, Dietmar; Radeglia, Reiner; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 38; nb. 12; (1983); p. 1591 - 1597 View in Reaxys With ferrocene in ethanol, Time= 0.166667h, Heating, hydrodediazoniation Wassmundt, Frederick W.; Kiesman, William F.; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8304 - 8308 View in Reaxys in N,N-dimethyl-formamide, Time= 2.5h, T= 0 - 20 °C , Inert atmosphere Lishchynskyi, Anton; Berthon, Guillaume; Grushin, Vladimir V.; Chemical Communications; vol. 50; nb. 71; (2014); p.

10237 - 10240 View in Reaxys With cyclohexa-1,4-diene in dimethylsulfoxide-d6, Time= 0.0166667h, T= 20 °C , Inert atmosphere Amaya, Toru; Hata, Dai; Moriuchi, Toshiyuki; Hirao, Toshikazu; Chemistry - A European Journal; vol. 21; nb. 46; (2015); p. 16427 - 16433 View in Reaxys

O

O N N

N

Br

O

O

HN Br

Rx-ID: 39819274 View in Reaxys 26/513 Yield

Conditions & References With methanesulfonic acid, carbon monoxide, tris-(o-tolyl)phosphine, palladium dichloride in water, acetonitrile, Time= 20h, T= 70 °C , Inert atmosphere Li, Wanfang; Wu, Xiao-Feng; Organic Letters; vol. 17; nb. 8; (2015); p. 1910 - 1913 View in Reaxys

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Br

Br

NH 2

Rx-ID: 40509762 View in Reaxys 27/513 Yield

Conditions & References Stage 1: With tetrafluoroboric acid, acetic acid, isopentyl nitrite in water, Time= 0.0833333h, T= 20 °C Stage 2: With eosin B disodium salt in N,N-dimethyl-formamide, Time= 0.5h, T= 18 °C , Inert atmosphere, Irradiation Majek, Michal; Filace, Fabiana; Von Wangelin, Axel Jacobi; Chemistry - A European Journal; vol. 21; nb. 12; (2015); p.

4518 - 4522 View in Reaxys

HO

Br

Rx-ID: 852431 View in Reaxys 28/513 Yield

Conditions & References With phosphorus pentabromide, bei der Destillation Riche; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 53; (1861); p. 588; Justus Liebigs Annalen der Chemie; vol. 121; (1862); p. 359 View in Reaxys With N-Bromosuccinimide, triphenylphosphine in dichloromethane, Time= 3h, T= 0 - 20 °C Bedford, Robin B.; Brenner, Peter B.; Carter, Emma; Gallagher, Timothy; Murphy, Damien M.; Pye, Dominic R.; Organometallics; vol. 33; nb. 21; (2014); p. 5940 - 5943 View in Reaxys Br

O Br

HO

Rx-ID: 29285428 View in Reaxys 29/513 Yield

Conditions & References With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] in toluene, Time= 20h, T= 140 °C Dupuy, Stephanie; Nolan, Steven P.; Chemistry - A European Journal; vol. 19; nb. 42; (2013); p. 14034 - 14038 View in Reaxys With silver(I) acetate, potassium carbonate in 1-methyl-pyrrolidin-2-one, Time= 16h, T= 120 °C , Inert atmosphere Goossen, Lukas J.; Linder, Christophe; Rodriguez, Nuria; Lange, Paul P.; Fromm, Andreas; Chemical Communications; nb. 46; (2009); p. 7173 - 7175 View in Reaxys With potassium carbonate in N,N-dimethyl acetamide, Time= 16h, T= 120 °C , chemoselective reaction Toy, Xiu Yi; Roslan, Irwan Iskandar Bin; Chuah, Gaik Khuan; Jaenicke, Stephan; Catalysis Science and Technology; vol.

4; nb. 2; (2014); p. 516 - 523 View in Reaxys With silver carbonate in dimethyl sulfoxide, T= 120 °C , Activation energy Grainger, Rachel; Cornella, Josep; Blakemore, David C.; Larrosa, Igor; Campanera, Josep M.; Chemistry - A European Journal; vol. 20; nb. 50; (2014); p. 16680 - 16687 View in Reaxys

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C

I

O

Br

Br

Br

O

Rx-ID: 36722399 View in Reaxys 30/513 Yield

Conditions & References

39 %

Typical procedure for formylation of aryl halides catalyzed byPdO/Co3O4(Table 2) General procedure: The suspension of 5 wtpercent PdO/Co3O4(20 mg, 1.6 molpercent Pd atomand 47 molpercent Co to substrate) in dioxane (1 mL) in a stainlessautoclave attached a glass tube was stirred at 120C under H2atmosphere (2 MPa) for 2 h.

After cooling to RT, aryl halide 1(0.5 mmol), K2CO3(0.5 mmol) and dioxane (1 mL) were added andstirred at 140C for 20 h under CO:H2= 3:1 atmosphere (4 MPa).The reaction mixture was analyzed by GC using tridecane (30 L,0.1 mmol) as an internal standard after filtration through celite toremove the catalyst. The products 2 and 3 were identified by com-parison of the retention time of GC with the authentic samples. Thealdehydes 2a–f and 2h–k were also characterized by1H and13CNMR after chromatographic purifications. Other aldehydes werefound to be difficult to isolate due to low yields and volatilities.

With hydrogen, potassium carbonate in 1,4-dioxane, Time= 20h, T= 120 - 140 °C , p= 30003Torr , Autoclave Hamasaki, Akiyuki; Yasutake, Yutaro; Norio, Takafumi; Ishida, Tamao; Akita, Tomoki; Ohashi, Hironori; Yokoyama, Takushi; Honma, Tetsuo; Tokunaga, Makoto; Applied Catalysis A: General; vol. 469; (2014); p. 146 - 152 View in Reaxys

O

O

I

Br

Br

Br

O

Rx-ID: 37172521 View in Reaxys 31/513 Yield 57 %

Conditions & References With 10% palladium on activated charcoal, 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, Time= 20h, T= 80 °C , Autoclave Yu, Bo; Zhao, Yanfei; Zhang, Hongye; Xu, Jilei; Hao, Leiduan; Gao, Xiang; Liu, Zhimin; Chemical Communications; vol.

50; nb. 18; (2014); p. 2330 - 2333 View in Reaxys Br

O

H B

Br

O

O Br

B

Br

O

Rx-ID: 37830126 View in Reaxys 32/513 Yield 79 %

Conditions & References With copper(l) iodide, iron(III)-acetylacetonate, N,N,N,N,-tetramethylethylenediamine, sodium hydride in tetrahydrofuran, mineral oil, T= -10 °C , Inert atmosphere Labre, Flavien; Gimbert, Yves; Bannwarth, Pierre; Olivero, Sandra; Dunach, Elisabet; Chavant, Pierre Y.; Organic Letters; vol. 16; nb. 9; (2014); p. 2366 - 2369 View in Reaxys

Br O

H B

Br

Br

O

Br

B

O

O

Rx-ID: 37830127 View in Reaxys 33/513

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Yield

Conditions & References

60 %

With copper(l) iodide, iron(III)-acetylacetonate, N,N,N,N,-tetramethylethylenediamine, sodium hydride in tetrahydrofuran, mineral oil, T= -10 °C , Inert atmosphere Labre, Flavien; Gimbert, Yves; Bannwarth, Pierre; Olivero, Sandra; Dunach, Elisabet; Chavant, Pierre Y.; Organic Letters; vol. 16; nb. 9; (2014); p. 2366 - 2369 View in Reaxys

(v5)(v5)(v5) (v4)(v5) C–

Si

Br

Br

(v10) Zr 4+ (v4)(v2) N – –C H– H– (v2) (v3)– H Ir3+ C – (v2) (v8) (v4) (v5)(v5) (v5) (v5)

(v5) (v5)

Br

(v5)

(v4)– C

Si

(v1)–

N–

Br

(v3) 4+ (v2) (v10) (v5)Zr– Br– –(v2) Br H (v1)–H 3+ (v8) Ir (v2) (v5)(v5) C –(v5) (v5) (v4)

(v3) – N

Br– Zr 4+ Si(v5) (v8) – C

(v1)

(v4) (v5)(v5) (v5)

Rx-ID: 38520228 View in Reaxys 34/513 Yield

Conditions & References

43 %, 19 %

in Cyclohexane-d12, Time= 10h, T= -78 - 70 °C Oishi, Masataka; Oshima, Masato; Suzuki, Hiroharu; Inorganic Chemistry; vol. 53; nb. 13; (2014); p. 6634 - 6654 View in Reaxys

Br

Rx-ID: 6416663 View in Reaxys 35/513 Yield

Conditions & References 7 : EXAMPLE 7 EXAMPLE 7 The procedure of Example 1 was repeated except that p-bromothiophenol was used in place of p-methylbenzyl mercaptan.

Bromobenzene was obtained in 77percent yield.

Patent; The British Petroleum Company p.l.c.; US4704481; (1987); (A) English View in Reaxys 2 : Bromobenzene: Bromobenzene: 100 ml Next, the reaction solution was heated to 130° C. under nitrogen flow, and stirred at this temperature (130° C.) for 6 hours.

After the end of the reaction, 50 ml of a saturated aqueous sodium thiosulfate solution was added to separate the liquid.

The aqueous layer was extracted 3 times with chloroform, and thereafter the solvent was distilled off with the organic layer.

Next, the obtained crystals were dissolved in toluene by heating, purified by column chromatography (chloroform/heptane=2:1), and then re-crystallized with chloroform/methanol, thereby obtaining 4.1 g (Yield: 75percent) of a yellow compound E8. in toluene Patent; CANON KABUSHIKI KAISHA; Kamatani, Jun; Yamada, Naoki; Kosuge, Tetsuya; Horiuchi, Takayuki; Nishide, Yosuke; Miyashita, Hirokazu; Saitoh, Akihito; US2013/33416; (2013); (A1) English View in Reaxys Bis[3,5-(1-methyl-o-carboranyl)m thyl]bromobenzene (26): Bis[3,5-(1-methyl-o-carboranyl)m thyl]bromobenzene (26): n-BuLi (5.2 mL, 1.6 M in hexane) was added dropwise to a solution of methyl-o-carborane (1.39 g, 8.80 mmol) in dry THF (80 mL), at a temperature between -5° and 0° C. under argon.

The mixture was stirred at this temperature range for 90 minutes, and then cooled to -15° to -20° C. (ice/salt bath).

A solution of Lil (0.166 g, 1.27 mmol) in dry THF (15 mL) and compound 25 (1.372 g, 4.00 mmol) was added, and the final reaction mixture was allowed to warm to room temperature and was stirred for 16 hours.

After the reaction was quenched with water, the resulting mixture was extracted with diethyl ether.

The organic extracts were washed once with water and once with brine, were dried over anhydrous Na2SO4, and the solvent was removed under vacuum.

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The crude product was purified by column chromatography using dichloromethane/petroleum ether 2:8 for elution, and the main product was collected and recrystallized from n-hexane to give 1.26 g (63percent yield) of the title compound; MS m/e 497.3; 1H-NMR (CDCl ) ′ ppm: 1.4-3.0 (br, 20H, BH), 2.17 (s, 6H, CH ), 3.43 (s, 4H, CH ), 6.96 (s, 1H), 7.31 (s, 2H).

3 3 2 Patent; Vicente, Maria da Graca Henriques; US2004/106592; (2004); (A1) English View in Reaxys With N-Bromosuccinimide, aluminium trichloride, bromine Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys Forrest,J.; Journal of the Chemical Society; (1960); p. 589 - 592 View in Reaxys Olah,G.A.; Tolgyesi,W.S.; Journal of Organic Chemistry; vol. 26; (1961); p. 2053 - 2055 View in Reaxys Wiegand,G.H.; McEwen,W.E.; Journal of Organic Chemistry; vol. 33; (1968); p. 2671 - 2675 View in Reaxys Wittig; Hoffmann; Chemische Berichte; vol. 95; (1962); p. 2729,2733 View in Reaxys McKillop et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 88 View in Reaxys Fry et al.; Journal of Organic Chemistry; vol. 35; (1970); p. 1232 View in Reaxys Rylski; Acta Poloniae Pharmaceutica; vol. 20; (1963); p. 156,160 View in Reaxys Akhtar; Oehlschlager; Tetrahedron; vol. 26; (1970); p. 3245,3250,3261 View in Reaxys Bunnett et al.; Chemical Communications (London); (1966); p. 367 View in Reaxys Korzeniowsky et al.; Journal of Organic Chemistry; vol. 42; (1977); p. 1469 View in Reaxys Davis et al.; Journal of Organic Chemistry; vol. 30; (1965); p. 415,416 View in Reaxys Hey; Tewfik; Journal of the Chemical Society; (1965); p. 2402 View in Reaxys Jones; Ritchie; Journal of the Chemical Society; (1960); p. 4141,4151 View in Reaxys Singh et al.; Chemistry and Industry (London, United Kingdom); (1977); p. 311 View in Reaxys Bartlett et al.; Journal of Organometallic Chemistry; vol. 46; (1972); p. 267 View in Reaxys Banerjee et al.; Journal of the Indian Chemical Society; vol. 56; (1979); p. 518 View in Reaxys Ol'dekop et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 48; (1978); p. 1591,1456 View in Reaxys Ponomarenko; Schindel'; Zhurnal Organicheskoi Khimii; vol. 2; (1966); p. 1450,1435 View in Reaxys Uemura et al.; Bulletin of the Chemical Society of Japan; vol. 47; (1974); p. 147 View in Reaxys Imai et al.; Journal of Organic Chemistry; vol. 42; (1977); p. 2309,2310, 2313 View in Reaxys Doyle et al.; Tetrahedron Letters; (1977); p. 2655 View in Reaxys Dorofeenko; Nauchnye Zapiski Luganskogo Sel'skokhozyaistvennogo Instituta; vol. 7; (1961); p. 203; ; vol. 58; nb. 2393g; (1963) View in Reaxys Patent; Bendix Co.; US3128240; (1959); ; vol. 61; nb. 610; (1964) View in Reaxys Zakharkin et al.; Doklady Chemistry; vol. 205; (1972); p. 551,552,554; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 205; (1972); p. 93 View in Reaxys

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Gokel et al.; Tetrahedron Letters; (1977); p. 1633 View in Reaxys Furuya et al.; Bulletin of the Chemical Society of Japan; vol. 41; (1968); p. 997,998 View in Reaxys Yoshida et al.; Tetrahedron Letters; (1978); p. 1809 View in Reaxys Lambert et al.; Journal of Organic Chemistry; vol. 30; (1965); p. 304,305 View in Reaxys Brackman; Smit; Recueil des Travaux Chimiques des Pays-Bas; vol. 85; (1966); p. 857,858 View in Reaxys Ogata et al.; Bulletin of the Chemical Society of Japan; vol. 37; (1964); p. 960 View in Reaxys Minisci; Gazzetta Chimica Italiana; vol. 90; (1960); p. 1307,1315 View in Reaxys Olah et al.; Journal of the American Chemical Society; vol. 86; (1964); p. 1046,1048 View in Reaxys Wolinski et al.; Roczniki Chemii; vol. 44; (1970); p. 905,906, 907 View in Reaxys Henry; Journal of Organic Chemistry; vol. 36; (1971); p. 1886,1888 View in Reaxys Kurz; Hage; Journal of Organic Chemistry; vol. 42; (1977); p. 4080 View in Reaxys Schteingarz et al.; Journal of Organic Chemistry USSR (English Translation); vol. 2; (1966); p. 703; Zhurnal Organicheskoi Khimii; vol. 2; (1966); p. 701 View in Reaxys Bhattacharya; Raj; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 15; (1977); p.

799 View in Reaxys Kabalka; Ferrell; Synthetic Communications; vol. 9; (1979); p. 443,446, 447 View in Reaxys Blum et al.; Journal of the American Chemical Society; vol. 89; (1967); p. 2338,2341 View in Reaxys Ohno; Tsuji; Journal of the American Chemical Society; vol. 90; (1968); p. 99 View in Reaxys McKillop et al.; Tetrahedron Letters; (1969); p. 1623 View in Reaxys Hradil; Chvalovsky; Collection of Czechoslovak Chemical Communications; vol. 33; (1968); p. 2029 View in Reaxys Cadogan et al.; Journal of the Chemical Society [Section] C: Organic; (1967); p. 1860 View in Reaxys Mukai et al.; Tetrahedron Letters; (1968); p. 1695 View in Reaxys Huyser; Wang; Journal of Organic Chemistry; vol. 33; (1968); p. 3901 View in Reaxys 5 : Coupling Reactions of But Ether and Bromobenzene EXAMPLE 5 Coupling Reactions of But Ether and Bromobenzene The General Procedure is repeated using bromobenzene as the aryl bromide.

The results are reported in Table 8.

Patent; The Dow Chemical Company; US5248829; (1993); (A) English View in Reaxys By following the procedures of Example 20A and substituting for 1-bromo-3-chlorobenzene with the following: ...

1-chloro-3-trifluoromethylbenzene; 1-chloro-3,4-methylenedioxybenzene; 1-chloro-3-methoxybenzene; 1-chlorobenzene; and 1-bromobenzene;

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Patent; Syntex U.S.A. Inc.; US5716954; (1998); (A) English View in Reaxys c : Notes c.

A catalytic amount (0.1 equivalents) of 1,4,7,10,13,16-hexaoxacyclooctadecane (18-Crown-6) was added to the reaction mixture.

The product was recrystallized from a mixture of pentane and diethyl ether.

The 4-[1-hydroxy-1-(3-(naphth-2-ylmethoxy)phenyl)ethyl]thiazole used as a starting material was obtained as follows: A solution of methyl 4-thiazolyl ketone (Chem. Abs, 89, 197387 y) in tetrahydrofuran was added to an equimolar amount of a Grignard reagent prepared by the reaction of 3-(naphth-2-ylmethoxy)bromobenzene and magnesium under tetrahydrofuran.

The reaction mixture was stirred at ambient temperature for 15 minutes, poured into a saturated ammonium chloride solution and extracted with ethyl acetate.

The organic layer was dried (MgSO4) and evaporated.

There was thus obtained the required starting material in 38percent yield as an oil.

The 2-(naphth-2-ylmethoxy)bromobenzene used as a starting material was obtained by the reaction of 2-bromomethylnaphthalene and 3-bromophenol using the conditions described in Example 1.

There was thus obtained the required bromobenzene in 68percent yield, m.p. 109°-111° C. (recrystallized from a mixture of ethanol and ethyl acetate).

Patent; ICI Pharma; Imperial Chemical Industries PLC; US5089513; (1992); (A) English View in Reaxys 1 : Coupling of Bromobenzene with Ethyl Acrylate; Aqueous DMF; KOAc EXAMPLE 1 Coupling of Bromobenzene with Ethyl Acrylate; Aqueous DMF; KOAc To a 100-mL, one-necked flask, equipped with a polytetrafluoroethylene-coated magnetic stirring bar, reflux condenser and thermometer well, is charged 10.71 g (0.1092 mol) of potassium acetate and 12.5 mL of deionized water.

After the potassium acetate has dissolved, 8.57 g (0.0546 mol) of bromobenzene, 5.46 g (0.546 mol) of ethyl acrylate, 0.0246 g (0.00011 mol) of palladium (II) acetate, 0.134 g (0.00044 mol) of tris-(o-tolyl)phosphine and 25 mL of N,N-dimethylformamide are added to the stirred mixture.

The atmosphere over the reaction mixture is purged with nitrogen and a nitrogen pad is maintained over the mixture throughout the reaction.

The mixture is stirred and heated at 90° C. for 16 hr.

Gas chromatographic analysis of the mixture shows that the mixture contains 96.5percent of ethyl 3-phenylpropenoate.

1 H NMR (CDCl ): ′ 7.6 (d, 1H, J=32 Hz); 6.4-7.4 (m, 5H), 6.3 (d, 1H, J=32 Hz), 4.2 (q, 2H, J=14 Hz), 1.3 (t, 3H, J=14 Hz).

3 Patent; The Dow Chemical Company; US5136069; (1992); (A) English View in Reaxys Formylation of bromobenzene with sodium formate as the hydrogen donor Formylation of bromobenzene with sodium formate as the hydrogen donor A mixture of 50 mg (0.05 mmol) of Pd(PPh3)4 and 400 mg (6 mmol) of sodium formate was placed in the reaction vessel.

After the mixture was purged with nitrogen, acetonitrile (4 mL), dimethyl sulfoxide (4 mL), and bromobenzene (0.1 mL, 0.95 mmol) were added via a syringe through a rubber septum.

Carbon monoxide (50 psi) was introduced at room temperature and the sealed reaction vessel was heated to 125° C. After 18 h the reaction mixture was cooled to room temperature, methanol (30 mL) was added, and benzaldehyde (63.7 mg, 0.60 mmol) was determined by HPLC in the crude filtered methanol solution.

Patent; State of Israel, Prime Minister's Office, Atomic Energy Commission; US4605749; (1986); (A) English View in Reaxys methyl ethyl ketone ... methyl isobutyl ketone cycloheptanone 1,3-dichlorobenzene propylbenzene bromobenzene 1,2-dibromobenzene 1,4-diethylbenzene methoxybenzene ...

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Patent; Eli Lilly and Company; US4303591; (1981); (A) English View in Reaxys Using the conditions analogous to those of Example 9, Mg is reacted with the following halides, ... butyl bromide; sec.-butyl iodide; isobutyl iodide; pentyl iodide; and phenyl bromide, Patent; Wisconsin Alumni Research Foundation; US4448721; (1984); (A) English View in Reaxys 23 : Example 23 Example 23 Bromination of Benzene 3.54 g (10 mmol) of F-TEDA-BF4fluorination agent, 1.0834 g (11 mmol) of NaBr, and 80 mL of acetonitrile were added to a 100-mL round bottom flask containing a magnetic stir bar and stirring was commenced.

To this was added 0.78 g (10 mmol) of benzene and the contents of the flask were stirred under nitrogen and sampled periodically.

After 72 hours of stirring at room temperature, analysis by GC-MS indicated that complete conversion of the benzene starting material had been achieved. GC-MS analysis showed a single product which was identified as bromobenzene. bromobenzene Patent; AIR PRODUCTS AND CHEMICALS, INC.; EP1138657; (2001); (A1) English View in Reaxys In addition, the following benzene derivatives are useful as monomeric substances of the present invention: ... acetophenone, benzylmethylether, benzylamine, thiophenol, bromobenzene, iodobenzene, o-dichlorobenzene, m-dichlorobenzene, ...

Patent; Hiratsuka, Atsunori; Yano, Kazuyoshi; Karube, Isao; Tsai, Shuo-Wen; Yokoyama, Kenji; Koide, Satoshi; Akimoto, Takuo; US2006/113189; (2006); (A1) English View in Reaxys O Br

Br

HO

Rx-ID: 33753234 View in Reaxys 36/513 Yield

Conditions & References With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] in N,N-dimethyl acetamide, Time= 20h, T= 165 °C Dupuy, Stephanie; Nolan, Steven P.; Chemistry - A European Journal; vol. 19; nb. 42; (2013); p. 14034 - 14038 View in Reaxys With dipotassium peroxodisulfate, silver(I) acetate in acetonitrile, Time= 24h, T= 100 °C Seo, Sangwon; Taylor, John B.; Greaney, Michael F.; Chemical Communications; vol. 48; nb. 66; (2012); p. 8270 - 8272 View in Reaxys

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Br

Br

Br

Br

F

Rx-ID: 35214699 View in Reaxys 37/513 Yield

Conditions & References

76 %

Stage 1: With n-butyllithium in tetrahydrofuran, hexane, T= 0 °C , Flow reactor Stage 2: With 2-fluoro-3,3-dimethyl-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide in tetrahydrofuran, hexane, T= 0 °C , Flow reactor Nagaki, Aiichiro; Uesugi, Yuki; Kim, Heejin; Yoshida, Jun-Ichi; Chemistry - An Asian Journal; vol. 8; nb. 4; (2013); p. 705 708 View in Reaxys

S

Br

S

S

Br

NH 2

Br

Rx-ID: 35563228 View in Reaxys 38/513 Yield

Conditions & References

25 %

Stage 1: With tetrafluoroboric acid, acetic acid, isopentyl nitrite in water, Time= 0.0833333h, T= 18 °C Stage 2: With eosin Y disodium salt in N,N-dimethyl-formamide, Time= 6h, T= 18 °C , Inert atmosphere, UV-irradiation, Schlenk technique, Concentration, Reagent/catalyst, Solvent Majek, Michal; Von Wangelin, Axel Jacobi; Chemical Communications; vol. 49; nb. 48; (2013); p. 5507 - 5509 View in Reaxys Br

O Br

HO

Rx-ID: 36588990 View in Reaxys 39/513 Yield

Conditions & References With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] in N,N-dimethyl acetamide, Time= 20h, T= 165 °C Dupuy, Stephanie; Nolan, Steven P.; Chemistry - A European Journal; vol. 19; nb. 42; (2013); p. 14034 - 14038 View in Reaxys

Br

Br

OH

Rx-ID: 37189614 View in Reaxys 40/513 Yield

Conditions & References With sodium perchlorate in acetonitrile, T= 25 °C , pH= 4.3, Kinetics, pH-value, Concentration O'Mahony, Michelle J.; More O'Ferrall, Rory A.; Boyd, Derek R.; Lam, Casey M.; O'Donoghue, Annmarie C.; Journal of Physical Organic Chemistry; vol. 26; nb. 12; (2013); p. 989 - 996 View in Reaxys

O–

F

I+ O

S

Br

F F

O

Rx-ID: 37681279 View in Reaxys 41/513

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Yield

Conditions & References General Procedure for Halogenation Reaction ofDiaryliodonium Salts with Cuprous Halide General procedure: A mixture of diaryliodonium salt (0.5 mmol), cuproushalide (0.75 mmol) and CH3CN (1mL) was taken in a 10mL reaction tube and heated at 80°C temperature for 2 hoursunder vigorous stirring. After completion of the reaction(observed on TLC or GC) the reaction mass was cooled toroom temperature, and 5 ml of water was added. The mixturewas stirred for 10 mins, the product was extracted with ethylacetate (3 * 10mL). The organic layer was washed withwater and dried over anhydrous sodium sulphate. Solventwas evaporated under reduced pressure to obtain the product.The crude product was purified on silica gel column by usingpetroleum ether and ethyl acetate as solvents to obtain thepure product. The obtained product was analyzed by 1HNMR, 13C NMR. With copper(I) bromide in acetonitrile, Time= 2h, T= 80 °C , Reagent/catalyst, Solvent, Temperature Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys

I+

O –O

S

Br

O

Rx-ID: 37681283 View in Reaxys 42/513 Yield

Conditions & References General Procedure for Halogenation Reaction ofDiaryliodonium Salts with Cuprous Halide General procedure: A mixture of diaryliodonium salt (0.5 mmol), cuproushalide (0.75 mmol) and CH3CN (1mL) was taken in a 10mL reaction tube and heated at 80°C temperature for 2 hoursunder vigorous stirring. After completion of the reaction(observed on TLC or GC) the reaction mass was cooled toroom temperature, and 5 ml of water was added. The mixturewas stirred for 10 mins, the product was extracted with ethylacetate (3 * 10mL). The organic layer was washed withwater and dried over anhydrous sodium sulphate. Solventwas evaporated under reduced pressure to obtain the product.The crude product was purified on silica gel column by usingpetroleum ether and ethyl acetate as solvents to obtain thepure product. The obtained product was analyzed by 1HNMR, 13C NMR. With copper(I) bromide in acetonitrile, Time= 2h, T= 80 °C Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys

I+ Br–

Br

Rx-ID: 37681285 View in Reaxys 43/513 Yield

Conditions & References General Procedure for Halogenation Reaction ofDiaryliodonium Salts with Cuprous Halide General procedure: A mixture of diaryliodonium salt (0.5 mmol), cuproushalide (0.75 mmol) and CH3CN (1mL) was taken in a 10mL reaction tube and heated at 80°C temperature for 2 hoursunder vigorous stirring. After completion of the reaction(observed on TLC or GC) the reaction mass was cooled toroom temperature, and 5 ml of water was added. The mixturewas stirred for 10 mins, the product was extracted with ethylacetate (3 * 10mL). The organic layer was washed withwater and dried over anhydrous sodium sulphate. Solventwas evaporated under reduced pressure to obtain the product.The crude product was purified on silica gel column by usingpetroleum ether and ethyl acetate as solvents to obtain thepure product. The obtained product was analyzed by 1HNMR, 13C NMR. With copper(I) bromide in acetonitrile, Time= 2h, T= 80 °C Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys

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I+ Cl –

Br

Rx-ID: 37681286 View in Reaxys 44/513 Yield

Conditions & References General Procedure for Halogenation Reaction ofDiaryliodonium Salts with Cuprous Halide General procedure: A mixture of diaryliodonium salt (0.5 mmol), cuproushalide (0.75 mmol) and CH3CN (1mL) was taken in a 10mL reaction tube and heated at 80°C temperature for 2 hoursunder vigorous stirring. After completion of the reaction(observed on TLC or GC) the reaction mass was cooled toroom temperature, and 5 ml of water was added. The mixturewas stirred for 10 mins, the product was extracted with ethylacetate (3 * 10mL). The organic layer was washed withwater and dried over anhydrous sodium sulphate. Solventwas evaporated under reduced pressure to obtain the product.The crude product was purified on silica gel column by usingpetroleum ether and ethyl acetate as solvents to obtain thepure product. The obtained product was analyzed by 1HNMR, 13C NMR. With copper(I) bromide in acetonitrile, Time= 2h, T= 80 °C Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys -1

F (v4)

F

B FF

Br I+

Rx-ID: 37681287 View in Reaxys 45/513 Yield

Conditions & References General Procedure for Halogenation Reaction ofDiaryliodonium Salts with Cuprous Halide General procedure: A mixture of diaryliodonium salt (0.5 mmol), cuproushalide (0.75 mmol) and CH3CN (1mL) was taken in a 10mL reaction tube and heated at 80°C temperature for 2 hoursunder vigorous stirring. After completion of the reaction(observed on TLC or GC) the reaction mass was cooled toroom temperature, and 5 ml of water was added. The mixturewas stirred for 10 mins, the product was extracted with ethylacetate (3 * 10mL). The organic layer was washed withwater and dried over anhydrous sodium sulphate. Solventwas evaporated under reduced pressure to obtain the product.The crude product was purified on silica gel column by usingpetroleum ether and ethyl acetate as solvents to obtain thepure product. The obtained product was analyzed by 1HNMR, 13C NMR. With copper(I) bromide in acetonitrile, Time= 2h, T= 80 °C Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys -1 I+

F F

F (v6)

F

Br

P F

F

Rx-ID: 37681288 View in Reaxys 46/513 Yield

Conditions & References General Procedure for Halogenation Reaction ofDiaryliodonium Salts with Cuprous Halide General procedure: A mixture of diaryliodonium salt (0.5 mmol), cuproushalide (0.75 mmol) and CH3CN (1mL) was taken in a 10mL reaction tube and heated at 80°C temperature for 2 hoursunder vigorous stirring. After completion of the reaction(observed on TLC or GC) the reaction mass was cooled toroom temperature, and 5 ml of water was added. The mixturewas stirred for 10 mins, the product was extracted with ethylacetate (3 * 10mL). The organic layer was washed withwater and dried over anhydrous sodium sulphate. Solventwas evaporated under reduced pressure to obtain the product.The crude product was purified on silica gel column by usingpetroleum ether and ethyl acetate as solvents to obtain thepure product. The obtained product was analyzed by 1HNMR, 13C NMR. With copper(I) bromide in acetonitrile, Time= 2h, T= 80 °C

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Li, Jian; Liu, Li; Ding, Dong; Sun, Jiang-Tao; Letters in Organic Chemistry; vol. 10; nb. 8; (2013); p. 541 - 548 View in Reaxys

O

HO B

O

Br

Br

HO

Br O

Br

OH

Br

O

Br

O

O Br

Rx-ID: 32726398 View in Reaxys 47/513 Yield

Conditions & References With 5-Nitro-1,10-phenanthroline, oxygen, palladium diacetate in N,N-dimethyl-formamide, Time= 24h, T= 80 °C , Heck reaction, chemoselective reaction Li, Yaming; Qi, Zisong; Wang, Huifeng; Fu, Xinmei; Duan, Chunying; Journal of Organic Chemistry; vol. 77; nb. 4; (2012); p. 2053 - 2057 View in Reaxys

Br

Br

O

Rx-ID: 32895090 View in Reaxys 48/513 Yield

Conditions & References With palladium diacetate in cyclohexane, Time= 24h, T= 140 °C , Molecular sieve, air Modak, Atanu; Deb, Arghya; Patra, Tuhin; Rana, Sujoy; Maity, Soham; Maiti, Debabrata; Chemical Communications; vol. 48; nb. 35; (2012); p. 4253 - 4255 View in Reaxys

F

F

F

F

(v1)

F F

F

F

F B

Cu

F

F

HO

F

F

I

Br

F F

HO

F F

F

Rx-ID: 33116760 View in Reaxys 49/513 Yield

Conditions & References

90 %Spectr. With air in dimethyl sulfoxide, Time= 12h, T= 20 °C Qi, Qingqing; Shen, Qilong; Lu, Long; Journal of the American Chemical Society; vol. 134; nb. 15; (2012); p. 6548 - 6551 View in Reaxys

O H 2N

O

Br

Br

Rx-ID: 33614328 View in Reaxys 50/513 Yield 40 %

Conditions & References Stage 1: With hydrogen bromide, sodium nitrite in water, T= -5 - 5 °C Stage 2: With copper(ll) bromide in water, acetone, T= 20 - 25 °C , Meerwein arylation

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Ostapiuk; Matiichuk; Pidlypnyi; Obushak; Russian Journal of Organic Chemistry; vol. 48; nb. 4; (2012); p. 519 - 522 View in Reaxys

I+

S HO

HO

Br–

OH

Br

Rx-ID: 34538010 View in Reaxys 51/513 Yield

Conditions & References With potassium thiocyanate in neat (no solvent), Microwave irradiation Vaddula, Buchi Reddy; Varma, Rajender S.; Leazer, John; European Journal of Organic Chemistry; nb. 35; (2012); p. 6852 6855 View in Reaxys

Br

Cl

Rx-ID: 32101527 View in Reaxys 52/513 Yield

Conditions & References With bromine, Time= 4h, T= 100 °C , Reflux, Ionic liquid Shi, Shen Yi; Kong, Ai Guo; Zhao, Xin Hua; Ding, Han Ming; Yang, Fan; Shan, Yong Kui; Chinese Chemical Letters; vol.

22; nb. 2; (2011); p. 147 - 150 View in Reaxys

HO B

Br

HO

Rx-ID: 853932 View in Reaxys 53/513 Yield

Conditions & References With N-Bromosuccinimide in acetonitrile, Time= 14h, T= 81 °C Thiebes, Christoph; Prakash, G. K. Surya; Petasis, Nicos A.; Olah, George A.; Synlett; nb. 2; (1998); p. 141 - 142 View in Reaxys With water, copper(ll) bromide Ainley; Challenger; Journal of the Chemical Society; (1930); p. 2171,2176 View in Reaxys With gold(III) chloride, N-Bromosuccinimide in 1,2-dichloro-ethane, Time= 24h, T= 60 °C Qiu, Di; Mo, Fanyang; Zheng, Zhitong; Zhang, Yan; Wang, Jianbo; Organic Letters; vol. 12; nb. 23; (2010); p. 5474 - 5477 View in Reaxys 2H

2H

2H

2H

2H

2H

Br

2H

2H

Br

2H

2H

2H

Rx-ID: 29400669 View in Reaxys 54/513 Yield 37.6 %Chromat.

Conditions & References With gold(III) chloride, N-Bromosuccinimide in dichloromethane, Time= 8h, T= 80 °C , Inert atmosphere Mo, Fanyang; Yan, Jerry Mingtao; Qiu, Di; Li, Fei; Zhang, Yan; Wang, Jianbo; Angewandte Chemie - International Edition; vol. 49; nb. 11; (2010); p. 2028 - 2032

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View in Reaxys -1

K+ -1

F (v4)

F

F

B FF

F

N+

Br

Br

Br

B

N

(v4)

F

Rx-ID: 29587317 View in Reaxys 55/513 Yield

Conditions & References

93 %Chromat.

With 10% palladium on activated carbon; Degussa type in methanol, Time= 1h, Reflux, Under air, Suzuki-Miyaura cross-coupling Hanna Jr., James M.; Varnedoe, Lee S.; Angel, Brad D.; McClellan, Joshua L.; Letters in Organic Chemistry; vol. 7; nb. 1; (2010); p. 1 - 6 View in Reaxys

Br

O

O

O

I

Br

Br

Br

F

I O

Rx-ID: 29825394 View in Reaxys 56/513 Yield

Conditions & References 9 :EXAMPLE 9; A solution of Kryptofix 2.2.2 (40 Ornol) in acetonitrile ( 1 mL) was added to a solution of KF (25 Qmol) in water (0.1 mL). The solvents were evaporated at 120° C and the residue was dried by azeotropic distillation with acetonitrile (3 X 1 mL). A solution of the phenyliodonium ylide precursor in dry dimethylformamide (1.0 mL) was added to the dried KFKryptofix complex and the reaction vessel was hermetically sealed. The reaction mixture was heated at 1300C for 15 min. The reaction mixture was cooled to room temperature and processed with a silica gel chromatography column (12 X 1 cm). The products of the reaction were eluted off the column with diethyl ether (20 mL) and analyzed by GC/MS (30 m X 0.25 mm J;W Scientific DB-5MS capillary column; Varian Saturn 2000 mass spectrometer) and by analytical HPLC (Phenomenex Luna Cl 8 column, 5μ particle size, 250 X 4.6 mm; eluent : methanol/water = 75/25; flow rate : 1 mL/min; UV detection at 254 nm).[0046] The products observed by GC/MS and analytical HPLC in these reactions are summarized in Figure 4.[0047] In each of these reactions with the fluoride ion, only three major aromatic products were observed - substitution of the nucleophile on the aromatic ring to yield a fluoroaryl derivative, substitution of hydrogen on the aromatic ring to give the arene and formation of an iodoaryl analog. GC/MS analysis conclusively proved the identity of these products. Analytical HPLC data supported the GC/MS data. The GC/MS analysis showed that the nucleophile (i.e. fluoride) did not substitute on the dione moiety to yield l-fluoro-2,2-dimethyl-l,3-dioxane-4,6-dione (13) (Figure 5, Path B) but instead the fluoride substituted regiospecifically on the phenyl ring on the ipso carbon. This observation can be rationalized by the presence of a delocalized negative charge distributed over the dione part of the dioxane ring system which would repel the nucleophile (i.e. fluoride ion) also carrying a negative charge.; On the other hand, the carbon atom on the aromatic ring carrying the positively charged iodine moiety has an electron deficiency and makes itself a more favorable point for the attack by the nucleophile to yield the fluoroaryl derivative (Figure 5, Path A). Substitution of hydrogen on the aromatic ring to give the hydrocarbon derivatives (i.e. benzene, toluene, mesitylene, anisole etc) strongly indicate involvement of a competing radical pathway for this nucleophilic substitution reaction and abstraction of hydrogen from the solvent. Such a radical pathway has previously been observed in the nucleophilic reaction of fluoride with the closely related iodonium salts (M. Van Der Puy, "Conversion of Diaryiodonium Salts to Aryl Fluorides." J. Flourine Chem. 21. pp 385-392 (1982)). Thus, when the trimethyl substituted iodonium ylide (10b) reaction was conducted in a deuterated solvent (e.g. DMF-d&7)

GC/MS analysis showed the presence of deutereomesitylene (Figure 4) in the product mixture indicating a radical channel competing with the nucleophilic substitution reaction.

With potassium fluoride, [2.2.2]cryptande in N,N-dimethyl-formamide, Time= 0.25h, T= 130 °C , sealed tube, Reactivity Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SATYAMURTHY, Nagichettiar; BARRIO, Jorge, R.; WO2010/117435; (2010); (A2) English View in Reaxys Br Br O Br

HO

Br

Rx-ID: 29888078 View in Reaxys 57/513

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Yield

Conditions & References With palladium(II) trifluoroacetate, silver carbonate in dimethyl sulfoxide, N,N-dimethyl-formamide, Time= 16h, T= 120 °C , Inert atmosphere Cornella, Josep; Lahlali, Hicham; Larrosa, Igor; Chemical Communications; vol. 46; nb. 43; (2010); p. 8276 - 8278 View in Reaxys

HO

F

Si

F

B HO

F

O

F F

Br

HO

F

Rx-ID: 29941045 View in Reaxys 58/513 Yield

Conditions & References

34 %Chromat., 17 %Chromat., 12 %Chromat.

With potassium fluoride, potassium phosphate, 1,10-Phenanthroline, copper(I) bromide in N,N-dimethyl-formamide, Time= 4h, T= 70 °C Chu, Lingling; Qing, Feng-Ling; Organic Letters; vol. 12; nb. 21; (2010); p. 5060 - 5063 View in Reaxys

N

Br

B N

Rx-ID: 30036243 View in Reaxys 59/513 Yield

Conditions & References With gold(III) chloride, N-Bromosuccinimide in 1,2-dichloro-ethane, Time= 24h, T= 60 °C Qiu, Di; Mo, Fanyang; Zheng, Zhitong; Zhang, Yan; Wang, Jianbo; Organic Letters; vol. 12; nb. 23; (2010); p. 5474 - 5477 View in Reaxys F

F

B–

K+

Br

F

Rx-ID: 30036246 View in Reaxys 60/513 Yield

Conditions & References With gold(III) chloride, N-Bromosuccinimide in 1,2-dichloro-ethane, Time= 24h, T= 60 °C Qiu, Di; Mo, Fanyang; Zheng, Zhitong; Zhang, Yan; Wang, Jianbo; Organic Letters; vol. 12; nb. 23; (2010); p. 5474 - 5477 View in Reaxys

(v2)

Au

(v4)

P

Br

Rx-ID: 31328079 View in Reaxys 61/513

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Yield

Conditions & References With N-Bromosuccinimide in deuterated benzene, T= 20 °C Hashmi, A. Stephen K.; Ramamurthi, Tanuja Dondeti; Todd, Matthew H.; Tsang, Althea S.-K.; Graf, Katharina; Australian Journal of Chemistry; vol. 63; nb. 12; (2010); p. 1619 - 1626 View in Reaxys

Br

Cl

Li

Br

Cl

Li

Rx-ID: 28241037 View in Reaxys 62/513 Yield

Conditions & References in tetrahydrofuran, biphenyl, pentane, T= -75.16 °C , Inert atmosphere, Equilibrium constant Gorecka-Kobylinska, Joanna; Schlosser, Manfred; Journal of Organic Chemistry; vol. 74; nb. 1; (2009); p. 222 - 229 View in Reaxys

Br

Br Br

Rx-ID: 4033243 View in Reaxys 63/513 Yield

Conditions & References 7 :Example 7; E1=H and X2Br in Formula (IV)The present invention was carried out using a microreactor apparatus, as shown in FIG. 2.A microsystem composed of two T-shaped micromixers (M1 and M2) and two microtube reactors (R1 and R2) was used.

The whole microsystem was dipped in a cooling bath (T° C.). A solution of o-dibromobenzene (0.27 M) in THF (flow rate: 6 mL/min, 1.62 mmol/min) and a solution of n-BuLi (1.5 M) in n-hexane (flow rate: 1.2 mL/min, 1.8 mmol/min) were introduced to the first T-shaped mixer M1 (inner diameter: 250 μm) by using syringe pumps. The resulting solution was passed through the microtube reactor R1 and was introduced to the second T-shaped mixer M2 (inner diameter: 500 μm). The solution was quenched with undiluted methanol (MeOH) (flow rate: 6 mL/min) and was introduced to the M2. The residence time of the tube reactor R1 (inner diameter: 500 μm, length=L cm) was X second. The residence time of the tube reactor R2 (inner diameter: 1,000 μm, length=50 cm) was 1.78 second. After finishing the reaction, an aliquot of the product solution was taken (15 sec) and was analyzed by GC (column, CBP1; 0.25 mm.x.25 m; initial oven temperature, 50° C.; rate of temperature increase, 10° C./ min). Table 3 shows the results obtained by the tests that were carried out changing the above-described temperature (T° C.), length of the first tube reactor R1 (L cm) and residence time (X sec).

Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 1.38889E-05 - 0.000455556h, T= -85 - -60 °C Stage 2: With methanol in tetrahydrofuran, hexane, Time= 0.000494444h, T= -85 - -60 °C , Product distribution / selectivity Patent; FUJIFILM Corporation; US2008/194816; (2008); (A1) English View in Reaxys With 9,10-anthraquinone radical anion in acetonitrile, Irradiation, other aryl halides, also aldehydes and ketones; var. quinone radical anions; var. solv.

Robertson, Peter K. J.; Eggins, Brian R.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 8; (1994); p. 1829 - 1832 View in Reaxys -1 F (v4)

F

B FF

Br Br

N+

I

Br

N

Rx-ID: 5057034 View in Reaxys 64/513 Yield 81 % Chromat.

Conditions & References With ferrocene, Iodoacetic acid in isopropyl alcohol, Time= 0.166667h, Heating, Iodination, hydrodediazoniation Wassmundt, Frederick W.; Kiesman, William F.; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8304 - 8308 View in Reaxys

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95 % Chromat.

With trimethylsilyl iodide, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, Time= 2h, T= 65 °C Hubbard, Abigail; Okazaki, Takao; Laali, Kenneth K.; Journal of Organic Chemistry; vol. 73; nb. 1; (2008); p. 316 - 319 View in Reaxys -1

F (v4)

F

B FF

Br

F

N

+

N

Rx-ID: 25932004 View in Reaxys 65/513 Yield

Conditions & References

96 % Chromat.

With trimethylsilyl bromide, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, Time= 2h, T= 55 °C , Schiemann reaction Hubbard, Abigail; Okazaki, Takao; Laali, Kenneth K.; Journal of Organic Chemistry; vol. 73; nb. 1; (2008); p. 316 - 319 View in Reaxys -1

F (v4)

F

B FF

Br

Br N+

Br

Br

N

Rx-ID: 25932009 View in Reaxys 66/513 Yield 67 % Chromat.

Conditions & References With trimethylsilyl bromide, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, T= 20 °C Hubbard, Abigail; Okazaki, Takao; Laali, Kenneth K.; Journal of Organic Chemistry; vol. 73; nb. 1; (2008); p. 316 - 319 View in Reaxys

Br

H 2N I

Br H N

H N

NH

Br

Rx-ID: 26033348 View in Reaxys 67/513 Yield 4.3 %, 3.7 %, 20.3 %

Conditions & References With dodecane, sodium t-butanolate, tris-(dibenzylideneacetone)dipalladium(0) in toluene, Time= 15h, T= 100 °C Jensen, Thomas; Pedersen, Henrik; Bang-Andersen, Benny; Madsen, Robert; Jorgensen, Morten; Angewandte Chemie International Edition; vol. 47; nb. 5; (2008); p. 888 - 890 View in Reaxys H N

Br

H 2N

Br

I

Rx-ID: 26033349 View in Reaxys 68/513 Yield 3.5 %

Conditions & References With dodecane, sodium t-butanolate, tris-(dibenzylideneacetone)dipalladium(0) in toluene, Time= 15h, T= 100 °C Jensen, Thomas; Pedersen, Henrik; Bang-Andersen, Benny; Madsen, Robert; Jorgensen, Morten; Angewandte Chemie International Edition; vol. 47; nb. 5; (2008); p. 888 - 890 View in Reaxys

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Br H N

Br

H 2N

Br

I

Rx-ID: 26033353 View in Reaxys 69/513 Yield 17.5 %

Conditions & References With dodecane, sodium t-butanolate, tris-(dibenzylideneacetone)dipalladium(0) in toluene, Time= 15h, T= 100 °C Jensen, Thomas; Pedersen, Henrik; Bang-Andersen, Benny; Madsen, Robert; Jorgensen, Morten; Angewandte Chemie International Edition; vol. 47; nb. 5; (2008); p. 888 - 890 View in Reaxys

Br

Rx-ID: 27843096 View in Reaxys 70/513 Yield

Conditions & References 1 :Example 1; Scrubbing Bromine from Gaseous HBr with DPE and FeCl3 Catalyst; In a 250 mL 3-neck flask with 14/20 joints, equipped with a condenser connected to a water trap, sparging tube, thermocouple, magnetic stirrer, and heated in a water bath were placed 3.1 g FeCl3 and 126.7 g DPE. This, at 60-62° C., was sparged with HBr gas for about 10 minutes then HBr was saturated with Br2 gas, before entering the DPE, by passing the HBr through a flask containing 18.5 mL Br2. The flask containing the Br2 was held in a water bath at room temperature. The HBr flow rate was about 100-200 mL/min. After about 2.5 hours all of the Br2 had been evaporate from its flask. The HBr flow was then stopped. The system was then purged with N2 for 30 minutes and then the DPE reaction mixture was poured into 300 mL water and stirred well. A sample of the organic phase was analyzed by GC using dibromomethane as solvent. GC analysis was on a 15 meter DB-5 column operated at 40° C., hold 2 min., then heated at 10° C. per min. to 300° C. The results are summarized in Table 1.

With hydrogen bromide, bromine, iron(III) chloride, Time= 2.66667h, T= 60 - 62 °C , Product distribution / selectivity Patent; Albemarle Corporation; US7408088; (2008); (B1) English View in Reaxys 7 :Example 7; Scrubbing Bromine from Gaseous HBr with DPE and FeCl3 </SUB; In this run, two 250 mL flasks were connected in series. The first flask was charged with 186.6 g of liquid Br&2.

The second with 105 g of DPE and 0.18 g of FeCl3 (black). N2, at a rate of about 300 mL/min

was swept through the first flask and into the second flask subsurface using a -inch (0.32 cm) O.D. diptube. All bromine was evaporated from the first flask over a period of 5.2 hours during which time the temperature of the second flask was maintained at 75-80° C. Formation of some solids on walls of the second flask was noted. All solids melted when the temperature was raised to about 95° C. A sample (0.8 g) of the product was taken for GC analysis. The results of this analysis are summarized in Table 5.

With bromine, iron(III) chloride, Time= 5.2h, T= 75 - 80 °C , Product distribution / selectivity Patent; Albemarle Corporation; US7408088; (2008); (B1) English View in Reaxys 3 :Example 3; Scrubbing Bromine from Gaseous HBr with DPE and 100 ppm of Iron as FeBr3 as Catalyst; In the flask described in Example 1 were placed 0.050 g FeBr3 and 0.085 g 60percent HBr. This was nitrogen purged at a rate of 15 mL/min for about 18 hours. DPE (120 grams) was added and this mixture was stirred at 52-60° C. and HBr was sparged in (250 mL/min) for about 10 minutes. Some of the FeBr3 remained undissolved but the DPE turned dark red. Br2 (17 ml) was added to a vessel through which the HBr passed before entering the DPE reactor. Over about 4.5 hours this bromine evaporated, during which time the reactor containing the DPE was held at 57-64° C. and the HBr at 240-250 mL/min. N2 (250 mL/min) was sparged in for 5 minutes and then 150 mL of water was added. The water trap, 1273 g, contained about 12 ppm Br2, and 13.7percent HBr. The reaction mixture, after stirring well, was phase separated and the organic phase was dried over CaCl2. GC of a sample of the organic phase showed the results summarized in Table 3.

With hydrogen bromide, bromine, ferric(III) bromide in water, Time= 4.66667h, T= 52 - 64 °C , Product distribution / selectivity

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Patent; Albemarle Corporation; US7408088; (2008); (B1) English View in Reaxys 2 :Example 2; Scrubbing Bromine from Gaseous HBr with DPE and Iron Water as a Catalyst System; In the apparatus described in Example 1 were placed 0.226 g of Fe powder and 0.41 g of 60percent aqueous HBr, followed by 91.2 g molten DPE. This was heated at 65° C. and HBr (250 mL/min) was sparged in for 30 minutes.

The mixture was light yellow in color and not all the Fe had dissolved. The feed of HBr was adjusted so that it passed first into a flask containing 41.7 g of Br&2 and

then into

the DPE mixture. The HBr flow was maintained at 240-250 mL/min. and the reactor containing the DPE was held at 62-66° C. After 3.7 hours all bromine had been evaporated by the HBr gas. HBr flow was continued for about 5 minutes and then the mixture was purged with N2 for about 10 minutes. The water trap was virtually colorless meaning that it contained <10 ppm Br2.

A sample of the reaction mixture were taken for NMR and GC analyses. The remainder were poured into water-containing about 4 mL of concentrated HCl. Much of the Fe powder remained unreacted. The pale yellow organic phase was phase separated, washed with water, and dried over CaCl2. The results of GC analysis, carried out as described in Example 1, are summarized in Table 2.

With hydrogen bromide, bromine, iron in water, Time= 4.28333h, T= 62 - 66 °C , Product distribution / selectivity Patent; Albemarle Corporation; US7408088; (2008); (B1) English View in Reaxys -1 F (v4)

HO

F

B FF

Br N+

Br

O

Br

Br

OH

N

Rx-ID: 28713026 View in Reaxys 71/513 Yield

Conditions & References With hydrogenchloride in water, T= 45 °C , Kinetics, Concentration, pH-value, Temperature Fernandez-Alonso, Alejandra; Bravo-Diaz, Carlos; Organic and Biomolecular Chemistry; vol. 6; nb. 21; (2008); p. 4004 4011 View in Reaxys

Br

Br

Br

Rx-ID: 4767832 View in Reaxys 72/513 Yield

Conditions & References

77 % Chromat.

With sodium hydride in tetrahydrofuran, Time= 1h, Heating Zhang, Wenming; Liao, Shijian; Xu, Yun; Zhang, Yiping; Synthetic Communications; vol. 27; nb. 22; (1997); p. 3977 - 3983 View in Reaxys With sodium hydrogencarbonate, N,N-dimethyl-formamide, palladium dichloride, Time= 48h, T= 150 °C Zawisza, Anna Maria; Muzart, Jacques; Tetrahedron Letters; vol. 48; nb. 38; (2007); p. 6738 - 6742 View in Reaxys H

H

H

H

H

H

Br

Br Br H

Br

Br

H Br

H Br

Br

Rx-ID: 10345114 View in Reaxys 73/513 Yield 24 %, 16 %

Conditions & References With hydrogen bromide, Time= 2h, T= 200 °C Su, Kuan-Jen; Mieusset, Jean-Luc; Arion, Vladimir B.; Brecker, Lothar; Brinker, Udo H.; Organic Letters; vol. 9; nb. 1; (2007); p. 113 - 115

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View in Reaxys H

H

H

H Br Br H

Br

Br

H

H Br

Rx-ID: 10407764 View in Reaxys 74/513 Yield

Conditions & References

33 %

in m-xylene, Time= 24h, Heating Su, Kuan-Jen; Mieusset, Jean-Luc; Arion, Vladimir B.; Brecker, Lothar; Brinker, Udo H.; Organic Letters; vol. 9; nb. 1; (2007); p. 113 - 115 View in Reaxys O

O

Br

O

HO Br

Br

Br

OH

O

Br

Rx-ID: 11163478 View in Reaxys 75/513 Yield

Conditions & References in acetonitrile, Irradiation Kosmrlj, Berta; Sket, Boris; Organic Letters; vol. 9; nb. 20; (2007); p. 3993 - 3996 View in Reaxys -1 F

F

2

B (v4)

F

Br

Br

F N

N+

N+

Br

N

Rx-ID: 11220507 View in Reaxys 76/513 Yield

Conditions & References

91 %

With dibenzo-18-crown-6, potassium bromide, copper(ll) bromide, 1,10-Phenanthroline, copper(I) bromide in acetonitrile, Time= 0.333333h, T= 20 °C , Sandmeyer bromination Beletskaya, Irina P.; Sigeev, Alexander S.; Peregudov, Alexander S.; Petrovskii, Pavel V.; Synthesis; nb. 16; (2007); p. 2534 - 2538 View in Reaxys O

F I+ F

B– F

F

O

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O

O

O

O

I

Br

Br

I

Rx-ID: 11234205 View in Reaxys 77/513 Yield

Conditions & References With BrNBu4 in chloroform, T= 55 °C Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys O

F I+ B–

F

F

F

O

Br

O

I

I

Br

Rx-ID: 11234210 View in Reaxys 78/513 Yield

Conditions & References With BrNBu4 in chloroform, T= 55 °C Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys -1

F (v4)

F

B FF

+I

Br

O

Br

I

O

I

O

Rx-ID: 11234212 View in Reaxys 79/513 Yield

Conditions & References With BrNBu4 in chloroform, T= 55 °C Fujita, Morifumi; Mishima, Eri; Okuyama, Tadashi; Journal of Physical Organic Chemistry; vol. 20; nb. 4; (2007); p. 241 244 View in Reaxys

Br

Br

Br Br

I

Rx-ID: 11253641 View in Reaxys 80/513 Yield 92 % Chromat.

Conditions & References Stage 1: With tert.-butyl lithium in tetrahydrofuran, diethyl ether, pentane, Time= 0.5h, T= -120 °C Stage 2: With iodine in tetrahydrofuran, diethyl ether, pentane, Time= 0.5h, T= -120 - -110 °C , Further stages.

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Bettinger, Holger F.; Filthaus, Matthias; Journal of Organic Chemistry; vol. 72; nb. 25; (2007); p. 9750 - 9752 View in Reaxys

Br

Br

Si

Si

Cl

Br

Rx-ID: 11253645 View in Reaxys 81/513 Yield

Conditions & References

40 % Chromat.

Stage 1: With tert.-butyl lithium in tetrahydrofuran, diethyl ether, pentane, Time= 0.5h, T= -120 °C Stage 2: in tetrahydrofuran, diethyl ether, pentane, Time= 0.5h, T= -120 - -110 °C , Further stages.

Bettinger, Holger F.; Filthaus, Matthias; Journal of Organic Chemistry; vol. 72; nb. 25; (2007); p. 9750 - 9752 View in Reaxys

HO

HO

Br

Br

Rx-ID: 23685149 View in Reaxys 82/513 Yield

Conditions & References

1.4 %, 28 % 5 Patent; Pfizer Inc; US2006/30714; (2006); (A1) English View in Reaxys

Br

Br O

HO

OH HO

HO

Br

Br

Rx-ID: 23738760 View in Reaxys 83/513 Yield

Conditions & References

1.7 - 5.5 %, 53.3 - 57.3 %, 6.4 10.6 %

6; 7 :EXAMPLE 6 The procedure of Example 3 was repeated using 1,4 dibromobenzene in place of 2,5-dibromopyridine. The major product was 4-(3-hydroxy-pentane-3-yl)-bromobenzene (57.3percent) indicating selective mono-lithiation. The product distribution is given in Table 2; EXAMPLE 7 The procedure of Example 4 was repeated using 1,4 dibromobenzene in place of 2,5-dibromopyridine. The temperature of the flow system was set at +100C. The flow rate of Stream A (n-BuLi) was 1.0 mL/min and the flow rate of Stream B (1,4-dibromobenzene/3-pentanone/THF) was 1.9 mL/min to give a reaction stream of 1.02 eq n-BuLi/1.0 eq 1,4-dibromobenzene/1.0 eq 3-pentanone. The major product was 4-(3-hydroxy-pentane-3-yl)-bromobenzene (53.3percent) indicating selective mono-lithiation. The product distribution is given in Table 2. The major product was isolated by column chromatography to afford a 35percent isolated yield. TABLE 2 4-(3-hydroxy- 1,4-di(3- 3- pentane- hydroxyhydroxy- 1,4 3-yl)- pentane- Reaction bromo- 3-ethyl- dibromo- bromo- 3-yl)- Type Solvent benzene heptane benzene benzene benzene Example Batch Toluene 1.1percent 28.0percent 68.8percent ?1.4percent 5 Example Batch THF 15.4percent? ?6.4percent ?2.8percent 57.3percent 1.7percent 6 Example Flow THF 6.5percent 10.6percent 18.2percent 53.3percent 5.5percent 7 With n-butyllithium in tetrahydrofuran, Time= 0.0833333 - 0.1h, T= 5 - 100 °C , Product distribution / selectivity Patent; Pfizer Inc; US2006/30714; (2006); (A1) English View in Reaxys H

N

O

Br

Mg

Br O

Rx-ID: 29006067 View in Reaxys 84/513

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Yield

Conditions & References 7 :7. Generation of an ether free solution composed of a Grignard reagent dissolved in an ionic liquid; [00062] To trihexyl(tetradecyl)phosphonium decanoate (5 mL) with a fewdrops of THF (up to 1 mL), commercially available 1 M phenylmagnesium bromide (5.0 mL) in THF was added at -78 °C. The mixture was stirred and warmed to room temperature. Tetrahydrofuran was removed in vacuo leaving a viscous pale yellow or orange solution to which hexanes (2.0 mL) was added to reduce viscosity.

Treatment of this solution with either bromine or N,N'-dimethylformamide followed by quenching with saturated aqueous ammonium chloride and addition of water followed by extraction with dichloromethane resulted in the formation of bromobenzene (98percent) and benzaldehyde (99percent), respectively, as determined by GC-MS studies.

Stage 1: in tetrahydrofuran, tetradecyl(trihexyl)phosphonium decanoate, T= -78 - 20 °C Stage 2: in tetradecyl(trihexyl)phosphonium decanoate, hexane, Product distribution / selectivity Patent; SIMON FRASER UNIVERSITY; WO2006/7703; (2006); (A1) English View in Reaxys Br

Br

Br

Rx-ID: 2006039 View in Reaxys 85/513 Yield

Conditions & References

73.3 % Chromat., 22.2 % Chromat.

With hydrogen bromide, dihydrogen peroxide, T= 50 °C , oth. temperature, var. stirring rate, var. ratio of reactants, E(activ.), ΔH(activ.), ΔS(activ.), ΔG(activ.), Product distribution, Kinetics, Thermodynamic data Salakhov, M. S.; Guseinov, M. M.; Chalabiev, Ch. A.; Mamedova, O. M.; J. Appl. Chem. USSR (Engl. Transl.); vol. 53; nb.

5; (1980); p. 1122 - 1126,885 - 888 View in Reaxys With hydrogenchloride, sodium hypochlorite, sodium bromide in water, Time= 5h, T= 19.85 °C , Product distribution, Further Variations: Temperatures Sadygov; Alimardanov; Chalabiev; Russian Journal of Organic Chemistry; vol. 41; nb. 11; (2005); p. 1631 - 1636 View in Reaxys -1

F

O

(v4)

F

B FF

N

N+

Br

H N

Br Br

N

Rx-ID: 9810106 View in Reaxys 86/513 Yield

Conditions & References

41 % Chromat.

T= 20 °C , Photolysis, Quantum yield Milanesi, Silvia; Fagnoni, Maurizio; Albini, Angeld; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 603 - 610 View in Reaxys

-1 F

Br

(v4)

F

B FF

I+

Br

I

I

Rx-ID: 9812209 View in Reaxys 87/513 Yield

Conditions & References With tetrabutylammomium bromide, tetrabutylammonium perchlorate in chloroform, T= 60 °C , Kinetics Fujita, Morifumi; Wan, Hyeok Kim; Fujiwara, Koji; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 480 - 488 View in Reaxys With tetrabutylammomium bromide, tetrabutylammonium perchlorate in chloroform, T= 60 °C

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Fujita, Morifumi; Wan, Hyeok Kim; Fujiwara, Koji; Okuyama, Tadashi; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 480 - 488 View in Reaxys -1 F (v4)

Si

B FF

F

N+

Br

Br

Br

N

Rx-ID: 9816635 View in Reaxys 88/513 Yield

Conditions & References

58 %

With xanth-9-one in acetonitrile, T= 20 °C , Photolysis Milanesi, Silvia; Fagnoni, Maurizio; Albini, Angeld; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 603 - 610 View in Reaxys

-1 F (v4)

B FF

F

Br

Br N+

Br

N

Rx-ID: 9819458 View in Reaxys 89/513 Yield

Conditions & References

54 %

With xanth-9-one in acetonitrile, T= 20 °C , Photolysis Milanesi, Silvia; Fagnoni, Maurizio; Albini, Angeld; Journal of Organic Chemistry; vol. 70; nb. 2; (2005); p. 603 - 610 View in Reaxys Br

Br

Br

Rx-ID: 10108703 View in Reaxys 90/513 Yield

Conditions & References

7.2 %, 78 % With hydrogenchloride, sodium hypochlorite, sodium bromide in water, Time= 5h, T= 19.85 °C , Product distribution, Further Variations: Temperatures, Reagents, reagents ratio Sadygov; Alimardanov; Chalabiev; Russian Journal of Organic Chemistry; vol. 41; nb. 11; (2005); p. 1631 - 1636 View in Reaxys

O

Br Br

C

O

Rx-ID: 9863880 View in Reaxys 91/513 Yield

Conditions & References T= 576.84 °C , IR laser powering, Product distribution, Further Variations: Reagents Hore, Nathan R.; Russell, Douglas K.; New Journal of Chemistry; vol. 28; nb. 5; (2004); p. 606 - 613 View in Reaxys

O

Br

C

O

Br

Rx-ID: 9863997 View in Reaxys 92/513 Yield

Conditions & References T= 576.84 °C , IR laser powering, Product distribution, Further Variations: Reagents

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Hore, Nathan R.; Russell, Douglas K.; New Journal of Chemistry; vol. 28; nb. 5; (2004); p. 606 - 613 View in Reaxys

I

Br

Br

Br

Br

Rx-ID: 5321989 View in Reaxys 93/513 Yield

Conditions & References With M2PtCl4 in N,N-dimethyl-formamide, T= 80 °C , Substitution, oxidative coupling, Kinetics Bezbozhnaya; Litvinenko; Skripnik; Zamashchikov; Russian Journal of General Chemistry; vol. 69; nb. 8; (1999); p. 1198 1203 View in Reaxys With sodium hydroxide, hydrazine hydrochloride, 10 wt. % palladium on activated carbon in toluene, Time= 24h, T= 25 °C , Product distribution Cellier, Pascal P.; Spindler, Jean-Francis; Taillefer, Marc; Cristau, Henri-Jean; Tetrahedron Letters; vol. 44; nb. 38; (2003); p. 7191 - 7195 View in Reaxys

O

HN H 2N Br

HO

H 2N

Br Br

OH

Br

HN

Br

Br

Rx-ID: 9480221 View in Reaxys 94/513 Yield

Conditions & References With bromine in dichloromethane, T= 10 - 25 °C , Title compound not separated from byproducts Soroka, Miroslaw; Goldeman, Waldemar; Malysa, Piotr; Stochaj, Monika; Synthesis; nb. 15; (2003); p. 2341 - 2344 View in Reaxys

P

Br

[(t-Bu)3P](Ph)PdBr

Rx-ID: 9504636 View in Reaxys 95/513 Yield

Conditions & References in benzene-d6, T= 70 °C , Equilibrium constant Roy, Amy H.; Hartwig, John F.; Journal of the American Chemical Society; vol. 125; nb. 46; (2003); p. 13944 - 13945 View in Reaxys H N Br

Rx-ID: 23936627 View in Reaxys 96/513 Yield 33%

Conditions & References 89 : Procedure for Amination of Bromobenzene Under an Air Atmosphere Example 89 Procedure for Amination of Bromobenzene Under an Air Atmosphere

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Copper (I) iodide (10 mg, 0.05 mmol, 5 mol percent), anhydrous fine powder potassium phosphate (425 mg, 2.0 mmol) and 2phenylphenol (34 mg, 0.2 mmol, 20 mol percent) were put into a screw-capped test tube with a Teflon septum.

Anhydrous toluene (1.0 mL), bromobenzene (105 μL, 1.0 mmol) and n-hexylamine (158 μL, 1.2 mmol) were added by microsyringe at room temperature under air atmosphere.

The reaction mixture was heated at 100° C. for 22 hours.

The reaction mixture was then allowed to reach room temperature.

Diethyl ether (2 mL), water (2 mL) and dodecane (internal standard, 227 μL) were added.

The organic layer was analyzed by GC to give 33percent GC yield of N-phenylhexylamine.

Patent; Buchwald, Stephen L.; Klapars, Artis; Antilla, Jon C.; Job, Gabriel E.; Wolter, Martina; Kwong, Fuk Y.; Nordmann, Gero; Hennessy, Edward J.; US2003/65187; (2003); (A1) English View in Reaxys

Br

O

I

Br O

Br

O

Rx-ID: 9086756 View in Reaxys 97/513 Yield

Conditions & References

10 % Chromat., 48 % Chromat.

With potassium tert-butylate, iron(II) bromide in dimethyl sulfoxide, Time= 1.5h

28 % Chromat., 2 % Chromat.

With potassium tert-butylate in dimethyl sulfoxide, Time= 3h, Irradiation

Baumgartner, Maria T.; Jimenez, Liliana B.; Pierini, Adriana B.; Rossi, Roberto A.; Journal of the Chemical Society. Perkin Transactions 2; nb. 6; (2002); p. 1092 - 1097 View in Reaxys

Baumgartner, Maria T.; Jimenez, Liliana B.; Pierini, Adriana B.; Rossi, Roberto A.; Journal of the Chemical Society. Perkin Transactions 2; nb. 6; (2002); p. 1092 - 1097 View in Reaxys

Li

Br

Br

Li

Rx-ID: 9260133 View in Reaxys 98/513 Yield

Conditions & References in tetrahydrofuran, T= -20 °C , Equilibrium constant, Further Variations: Temperatures Reich, Hans J.; Gudmundsson, Birgir Oe.; Green, D. Patrick; Bevan, Martin J.; Reich, Ieva L.; Helvetica Chimica Acta; vol. 85; nb. 11; (2002); p. 3748 - 3772 View in Reaxys

Br

Br

Br

Br Br

Rx-ID: 3918776 View in Reaxys 99/513 Yield

Conditions & References With oxygen, potassium bromide, sodium nitrite in water, trifluoroacetic acid, Time= 24h, T= 20 °C , Product distribution Cheprakov, A. V.; Makhon'kov, D. I.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 2; (1988); p. 217 - 223; Zhurnal Organicheskoi Khimii; vol. 24; nb. 2; (1988); p. 248 - 255 View in Reaxys

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With hydrogen bromide, oxygen, ruthenium trichloride, Time= 17h, T= 145 °C , p= 750.075Torr Limberg, Christian; Teles, Joaquim Henrique; Advanced Synthesis and Catalysis; vol. 343; nb. 5; (2001); p. 447 - 449 View in Reaxys

O

O SiH

O I

O

Br

Br

O

Si

Br

O

Rx-ID: 8938396 View in Reaxys 100/513 Yield

Conditions & References With N-ethyl-N,N-diisopropylamine, johnphos, bis(dibenzylideneacetone)-palladium(0) in 1-methyl-pyrrolidin-2-one, Time= 2h, T= 20 °C

68 %

Manoso; DeShong; Journal of Organic Chemistry; vol. 66; nb. 22; (2001); p. 7449 - 7455 View in Reaxys

Br

N

O

Br

OH

O Br

O N

HO

O

Rx-ID: 8643581 View in Reaxys 101/513 Yield

Conditions & References in acetonitrile, T= 20 °C , Irradiation, photolysis, Product distribution, Further Variations: Reaction partners Hashimoto, Ji-Ichiro; Segawa, Katsunori; Itoh, Hiroki; Sakuragi, Hirochika; Chemistry Letters; nb. 4; (2000); p. 362 - 363 View in Reaxys O O S

Br–

N–

N+

N+

N

Br

S O O

O

O

O

O

O

O

S

S

S

N

N–

N S

S

O

O

O

O

O

N+

S O

Rx-ID: 5201334 View in Reaxys 102/513 Yield 2 %, 1 %

Conditions & References in acetonitrile, Time= 0.75h, T= 60 °C , Substitution Barbero; Degani; Dughera; Fochi; Journal of Organic Chemistry; vol. 64; nb. 10; (1999); p. 3448 - 3453 View in Reaxys

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O O S N–

N

N+

N

S O O

O

O

O

H N

O

S

O S

N

Br

N S

S

O

O O

O

Rx-ID: 5219391 View in Reaxys 103/513 Yield

Conditions & References

2 %, 1 %, 1 %

With tetrabutylammomium bromide, Time= 0.75h, T= 60 °C , Substitution, Product distribution, Further Variations: various reagent ratios Barbero; Degani; Dughera; Fochi; Journal of Organic Chemistry; vol. 64; nb. 10; (1999); p. 3448 - 3453 View in Reaxys O O S N–

N

N+

Br

S O O

Rx-ID: 5222381 View in Reaxys 104/513 Yield

Conditions & References With tetrabutylammomium bromide, copper in acetonitrile, T= 20 °C , Substitution, Product distribution, Further Variations: Temperatures, various reagent ratios Barbero; Degani; Dughera; Fochi; Journal of Organic Chemistry; vol. 64; nb. 10; (1999); p. 3448 - 3453 View in Reaxys Br O

O Br

O

Rx-ID: 5021031 View in Reaxys 105/513 Yield

Conditions & References in dichloromethane-d2, T= -15 °C Berger, Christian; Dieterich, Stefan; Dilger, Ulrich; Geuenich, Daniel; Helios, Heike; Herges, Rainer; Kirchmer, Peter; Roettele, Herbert; Schroeder, Gerhard; Angewandte Chemie - International Edition; vol. 37; nb. 13-14; (1998); p. 1854 1857 View in Reaxys in dichloromethane-d2, T= -15 °C , half-life; further temperatures, Thermodynamic data Berger, Christian; Dieterich, Stefan; Dilger, Ulrich; Geuenich, Daniel; Helios, Heike; Herges, Rainer; Kirchmer, Peter; Roettele, Herbert; Schroeder, Gerhard; Angewandte Chemie - International Edition; vol. 37; nb. 13-14; (1998); p. 1854 1857 View in Reaxys

HO

OH

Br

Br

Br

Rx-ID: 24653943 View in Reaxys 106/513

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Yield

Conditions & References 1 : Preparation of Compound 11 STR4 EXAMPLE 1 Preparation of Compound 11 STR4 To a solution of bromohydroquinone (10.0 g, 0.053 mol) in DMF (70 mL) was added 1-bromopropane (39.0 g, 0.318 mol) and cesium carbonate (50 g, 0.153 mol) and heated at 90° C. for 2 days.

The reaction mixture was filtered through Celite and washed with ethyl acetate (500 mL).

The solution was concentrated and chromatographed on silica gel eluding with 0.25percent ethyl acetate-hexane to yield 9.0 g (62percent) of the bromobenzene (136) as a colorless oil; 1 H NMR (500 MHz, CDCl3)(136) ′ 7.08(d, 1H), 6.80 (dd,1H), 6.77(dd,1H), 4.00(q,2H), 3.93(q,2H), 1.40(t,3H), 1.38 (t,3H).

With caesium carbonate in N,N-dimethyl-formamide Patent; Vertex Pharmaceuticals Inc.; US5717092; (1998); (A) English View in Reaxys

Br–

2 Bi5+

Br

C–

3

Bi

Bi

Rx-ID: 26090366 View in Reaxys 107/513 Yield

Conditions & References

99 %

in toluene, solvent removing, crystals washing and drying Sharutin, V. V.; Sharutina, O. K.; Egorova, I. V.; Panova, L. P.; Russian Journal of General Chemistry; vol. 68; (1998); p.

318 - 319; Zhurnal Obshchei Khimii; vol. 68; (1998); p. 345 - 346 ; (from Gmelin) View in Reaxys

Br–

2

3

C– Bi

Sb5+

Br

Br

Sb

Bi

Rx-ID: 26672082 View in Reaxys 108/513 Yield 96 %, 86 %

Conditions & References in toluene, 0.5 h, 20°C; solvent and bromobenzene removing, crystals washing (petroleum ether) and drying, Ph4SbBr in residue, Ph3Bi in petroleum ether soln.

Sharutin, V. V.; Sharutina, O. K.; Egorova, I. V.; Panova, L. P.; Russian Journal of General Chemistry; vol. 68; (1998); p.

318 - 319; Zhurnal Obshchei Khimii; vol. 68; (1998); p. 345 - 346 ; (from Gmelin) View in Reaxys

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-1

O

F (v4)

F

B FF

O

N+

Br

Br

O

Br

N

O

Rx-ID: 4741195 View in Reaxys 109/513 Yield

Conditions & References in acetonitrile, T= -48 °C , Irradiation, Yield given. Yields of byproduct given Kosynkin; Bockman; Kochi; Journal of the American Chemical Society; vol. 119; nb. 21; (1997); p. 4846 - 4855 View in Reaxys

F

F Br F

Br

F

Br

F

F

F F

Rx-ID: 4812646 View in Reaxys 110/513 Yield

Conditions & References Time= 24h, Irradiation, Product distribution Song, Yong-Qi; Yuzuri, Tomoaki; Suezawa, Hiroko; Sakakibara, Kazuhisa; Hirota, Minoru; Nakada, Masahiro; Bulletin of the Chemical Society of Japan; vol. 70; nb. 8; (1997); p. 1875 - 1878 View in Reaxys -1 F (v4)

HO

F

B FF

Br N+

Br

O

Br

N

Rx-ID: 5047533 View in Reaxys 111/513 Yield

Conditions & References

20 % Chromat.

With Iodoacetic acid, Time= 0.166667h, Heating, Etherification, hydrodediazoniation Wassmundt, Frederick W.; Kiesman, William F.; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8304 - 8308 View in Reaxys -1 F (v4)

OH

F

B FF

I

Br N+

Br

Br

O

Br

N

Rx-ID: 5051306 View in Reaxys 112/513 Yield

Conditions & References

58 % Chromat., 11 % Chromat.

With Iodoacetic acid, Time= 0.166667h, Heating, Etherification, iodination; hydrodediazoniation Wassmundt, Frederick W.; Kiesman, William F.; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8304 - 8308 View in Reaxys -1 F F

N

N+

Br

F (v6)

F

P

Br

F F

Rx-ID: 5059210 View in Reaxys 113/513

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Yield

Conditions & References in various solvent(s), hydrodediazoniation Wassmundt, Frederick W.; Kiesman, William F.; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8304 - 8308 View in Reaxys -1 F F N+

N

Br

F (v6)

F

P

I

Br

Br

F F

Rx-ID: 5059211 View in Reaxys 114/513 Yield 65 % Chromat.

Conditions & References With ferrocene, Iodoacetic acid in various solvent(s), Iodination, hydrodediazoniation Wassmundt, Frederick W.; Kiesman, William F.; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8304 - 8308 View in Reaxys Br

HO

O

Br Br

Br

Rx-ID: 24573503 View in Reaxys 115/513 Yield

Conditions & References 14.a : 3-[1-(3,4-Dichlorophenyl)-3-(4-(2-hydroxyphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride a.

2-Benzyloxybromobenzene. A solution of 2-bromophenol (17.3 g) in dimethylformamide (200 mL) was treated with potassium carbonate (15.2 g) followed by benzyl bromide (17.1 g, 11.9 mL).

After stirring for 3 hours at the room temperature, the reaction mixture was diluted water and hexane.

The aqueous layer was extracted with hexane; and the organic layers were washed (water, 1N sodium hydroxide, brine), dried and evaporated to give the product as a colorless oil (22.94 g).

This material was fractionally distilled under reduced pressure to afford the bromobenzene (16.52 g); bp 110°-145° C. (1333 Pa); NMR (CDCl3): 5.17 (s,2), 6.65 (d of t,1, J=8, J=1), 6.92-6.96 (d of d,1, J=8, J=1), 7.19-7.26 (m,1), 7.33-7.42 (m,3), 7.46-7.50 (m,2), 7.55 (d of d,1, J=9, J=2).

This material was used in the next step without further purification.

With potassium carbonate in N-methyl-acetamide Patent; Zeneca Limited; US5589489; (1996); (A) English View in Reaxys 6.a : a. a.

2-Benzyloxybromobenzene A solution of 2-bromophenol (17.3 g) in dimethylformamide (200 mL) was treated with potassium carbonate (15.2 g) followed by benzyl bromide (17.1 g, 11.9 mL).

After stirring for 3 hours at the room temperature, the reaction mixture was diluted water and hexane.

The aqueous layer was extracted with hexane; and the organic layers were washed (water, 1N sodium hydroxide, brine), dried and evaporated to give the product as a colorless oil (22.94 g).

This material was fractionally distilled under reduced pressure to afford the bromobenzene (16.52 g); bp 110°-145° C. (1333 Pa); NMR (CDCl3): 5.17 (s,2), 6.65 (d of t,1, J=8, J=1), 6.92-6.96 (d of d, 1, J=8, J=1), 7.19-7.26 (m, 1), 7.33-7.42 (m, 3), 7.46-7.50 (m, 2), 7.55 (d of d, 1, J=9, J=2).

This material was used in the next step without further purification.

With potassium carbonate in N-methyl-acetamide Patent; Zeneca Limited; US5654299; (1997); (A) English View in Reaxys

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O

Br

OH

Br

Br Br

Rx-ID: 24573546 View in Reaxys 116/513 Yield

Conditions & References 12.a : 3-[1-(3,4-Dichlorophenyl)-3-(4-(4-hydroxyphenyl)piperidino)propyl]-2-methyl-2,3-dihydroisoindol-1-one hydrochloride a.

4-Benzyloxybromobenzene. A solution of 4-bromophenol (17.3 g) in dimethylformamide (200 mL) was treated with potassium carbonate (15.2 g) followed by benzyl bromide (17.1 g 11.9 mL).

After stirring for 16 hours at ambient temperature, the reaction mixture was diluted with water and hexane.

The aqueous layer was extracted with hexane:ether (5:1).

The organic extracts were washed (water, 1N sodium hydroxide, brine), dried and evaporated to give the bromobenzene as a white solid (23.4 g); NMR (CDCl3): 5.03 (s,2), 6.85 (dd,2, J1 =5, J2 =2), 7.3-7.4 (m,7); MS: m/z=263(M+1).

This material was used in the next step without further purification.

With potassium carbonate in N-methyl-acetamide Patent; Zeneca Limited; US5589489; (1996); (A) English View in Reaxys 5.a : a. a.

4-Benzyloxybromobenzene A solution of 4-bromophenol (17.3 g) in dimethylformamide (200 mL) was treated with potassium carbonate (15.2 g) followed by benzyl bromide (17.1 g 11.9 mL).

After stirring for 16 hours at ambient temperature, the reaction mixture was diluted with water and hexane.

The aqueous layer was extracted with hexane:ether (5:1).

The organic extracts were washed (water, 1N sodium hydroxide, brine), dried and evaporated to give the bromobenzene as a white solid (23.4 g); NMR (CDCl3): 5.03 (s,2), 6.85 (dd, 2, J1 =5, J2 =2), 7.3-7.4 (m, 7); MS: m/z=263(M+1).

This material was used in the next step without further purification.

With potassium carbonate in N-methyl-acetamide Patent; Zeneca Limited; US5654299; (1997); (A) English View in Reaxys

Br

Br

Br Br

Br Br

Br

Br

Br Br

Rx-ID: 4517140 View in Reaxys 117/513 Yield 3 % Chromat., 1 % Chromat., 42 % Chromat., 30 % Chromat.

Conditions & References With potassium hydroxide, hydrogen, 10 wt. % palladium on activated carbon in 2,2,4-trimethylpentane, Time= 0.666667h, T= 50 °C , var. cat.: Raney-Ni, add. of Aliquat 336, Product distribution Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro; Gazzetta Chimica Italiana; vol. 126; nb. 6; (1996); p. 317 - 328 View in Reaxys

Br– N+

N Si

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O

H N

O

H 2N

Br

Rx-ID: 4568699 View in Reaxys 118/513 Yield

Conditions & References With nitrosonium tetrafluoroborate, multistep r., 1.) CH2Cl2, -78 deg C, 2 h; 2.) CH2Cl2, CH3CN, r.t., 1 h; nitrosation products depend on reaction conditions and type of the nucleophile, Product distribution Alvarez, Roberto Martinez; Vazquez, Angel Sanchez; Hananck, Michael; Subramanian; Journal of Physical Organic Chemistry; vol. 9; nb. 4; (1996); p. 227 - 233 View in Reaxys

Br

14C

Br

Li

O

Li

O

As

14C

Li

14

C As

Rx-ID: 4673144 View in Reaxys 119/513 Yield

Conditions & References T= 24.9 °C , E; ΔG(excit.), Rate constant Batalov; Pogodina; Russian Journal of General Chemistry; vol. 66; nb. 1; (1996); p. 92 - 94 View in Reaxys

Br

14C

Br

O

Li

O

N

Li

14C

Li

14C

N

Rx-ID: 4675132 View in Reaxys 120/513 Yield

Conditions & References T= 24.9 °C , E; ΔG(excit.), Rate constant

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Batalov; Pogodina; Russian Journal of General Chemistry; vol. 66; nb. 1; (1996); p. 92 - 94 View in Reaxys

Br

14C

Br

Li

O

Li

O

Bi

14C

Li

14C

Bi

Rx-ID: 4675309 View in Reaxys 121/513 Yield

Conditions & References T= 24.9 °C , E; ΔG(excit.), Rate constant Batalov; Pogodina; Russian Journal of General Chemistry; vol. 66; nb. 1; (1996); p. 92 - 94 View in Reaxys

Br

14C

Li

O

Br

O

Li

14C

Rx-ID: 4675310 View in Reaxys 122/513 Yield

Conditions & References T= 24.9 °C , E; ΔG(excit.), Rate constant Batalov; Pogodina; Russian Journal of General Chemistry; vol. 66; nb. 1; (1996); p. 92 - 94 View in Reaxys With triphenylantimony, T= 24.9 °C , E; ΔG(excit.), Rate constant Batalov; Pogodina; Russian Journal of General Chemistry; vol. 66; nb. 1; (1996); p. 92 - 94 View in Reaxys

Br

14C

P

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O

54/149

Li

2018-06-17 20:49:04

Br

Li

O

14C

14C

Li

P

Rx-ID: 4691328 View in Reaxys 123/513 Yield

Conditions & References T= 24.9 °C , E; ΔG(excit.), Rate constant Batalov; Pogodina; Russian Journal of General Chemistry; vol. 66; nb. 1; (1996); p. 92 - 94 View in Reaxys N N+ O O

Br

–

O

Cl

O

Rx-ID: 4064608 View in Reaxys 124/513 Yield

Conditions & References

4 %, 34 %

With triethylamine hydrobromide, 1,2-dichloro-ethane, Time= 2h, T= 80 °C , Product distribution, Mechanism Christopher Buxton; Fensome, Mark; Heaney, Harry; Mason, Kenneth G.; Tetrahedron; vol. 51; nb. 10; (1995); p. 2959 2968 View in Reaxys

Si

C

Br

Br

Si

Si –O

Br

O–

Rx-ID: 4255268 View in Reaxys 125/513 Yield

Conditions & References With hydroxide, T= 24.9 °C , p= 0.4Torr , ΔH(acid), Thermodynamic data, Product distribution Wenthold; Squires; Journal of Mass Spectrometry; vol. 30; nb. 1; (1995); p. 17 - 24 View in Reaxys Br

Br

C

Br

Si

Si

Si

–O

O–

Rx-ID: 4255658 View in Reaxys 126/513 Yield

Conditions & References With hydroxide, T= 24.9 °C , p= 0.4Torr , ΔH(acid), Thermodynamic data, Product distribution Wenthold; Squires; Journal of Mass Spectrometry; vol. 30; nb. 1; (1995); p. 17 - 24 View in Reaxys

Si Br

Br

Si

Si O–

O

Br

–

Rx-ID: 4256308 View in Reaxys 127/513

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Yield

Conditions & References With hydroxide, T= 24.9 °C , p= 0.4Torr , ΔH(acid), Thermodynamic data, Product distribution Wenthold; Squires; Journal of Mass Spectrometry; vol. 30; nb. 1; (1995); p. 17 - 24 View in Reaxys

Br Si

Br

Si Si O–

O–

Br

Rx-ID: 4275824 View in Reaxys 128/513 Yield

Conditions & References With hydroxide, T= 24.9 °C , p= 0.4Torr , ΔH(acid), Thermodynamic data, Product distribution Wenthold; Squires; Journal of Mass Spectrometry; vol. 30; nb. 1; (1995); p. 17 - 24 View in Reaxys

O

F

O

F –Si

O

F O

O

Br

O

O

Br

O

K+

Rx-ID: 4287705 View in Reaxys 129/513 Yield

Conditions & References With N-Bromosuccinimide in tetrahydrofuran, T= 10 °C , relative reactivity of two aryl groups, Product distribution Tamao, Kohei; Hayashi, Takashi; Ito, Yoshihiko; Bulletin de la Societe Chimique de France; vol. 132; (1995); p. 556 - 558 View in Reaxys

F O

F

Br Br

S O

F O

Rx-ID: 4345493 View in Reaxys 130/513 Yield

Conditions & References With triethylsilane, palladium diacetate, 1,3-bis-(diphenylphosphino)propane in N,N-dimethyl-formamide, Time= 1h, T= 43 °C Kotsuki; Datta; Hayakawa; Suenaga; Synthesis; nb. 11; (1995); p. 1348 - 1350 View in Reaxys

Br

Br

Br

Rx-ID: 2011109 View in Reaxys 131/513 Yield

Conditions & References With tetrabutoxytitanium, diisobutylaluminium hydride in diethyl ether, Time= 6h, Heating Dzhemilev, U. M.; Gaisin, R. L.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 37; nb. 10; (1988); p. 2099 - 2102; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1988); p.

2332 - 2334 View in Reaxys With hydrogenchloride, calcium UFP, 1.) THF, 10 deg C, 2 h, 2.) hydrolysis, Yield given. Multistep reaction

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Mochida, Kunio; Ogura, Sei-ichi; Yamanishi, Takayuki; Bulletin of the Chemical Society of Japan; vol. 59; nb. 8; (1986); p.

2633 - 2634 View in Reaxys With sodium bis(2-methoxyethoxy)aluminium dihydride in toluene, T= 70 °C , Rate constant Vcelak, Jaroslav; Friesova, Anna; Rericha, Roman; Hetflejs, Jiri; Collection of Czechoslovak Chemical Communications; vol. 59; nb. 6; (1994); p. 1368 - 1383 View in Reaxys

HS Br

S

S

Br

S

Rx-ID: 2397983 View in Reaxys 132/513 Yield

Conditions & References

24 %, 7 %

With CoCl2 in acetonitrile, Time= 1h, Irradiation, further with pyridine, var. of benzyl halogenide, thiol, Product distribution Chowdhury, Shantanu; Samuel, Purnima M.; Das, Indira; Roy, Sujit; Journal of the Chemical Society, Chemical Communications; nb. 17; (1994); p. 1993 - 1994 View in Reaxys Cl Br

Cl Cl

Br–

N

N+

Br

Cl Cl

Cl

Rx-ID: 4249613 View in Reaxys 133/513 Yield

Conditions & References

33 %

With potassium bromide, copper(ll) bromide in water, acetone, Time= 1.5h, T= 5 - 10 °C Grishchuk, B. D.; Kudrik, E. Ya.; Gorbovoi, P. M.; Garmider, V. L.; Ganushchak, N. I.; Russian Journal of General Chemistry; vol. 64; nb. 8.1; (1994); p. 1164 - 1166; Zhurnal Obshchei Khimii; vol. 64; nb. 8; (1994); p. 1294 - 1297 View in Reaxys

O

Br

O

O

Rx-ID: 24448027 View in Reaxys 134/513 Yield 60%

Conditions & References 43 : EXAMPLE 43 n-Butyl-lithium (1.5M in hexane, 26 ml) was added dropwise to a stirred solution of a portion (7.3 g) of the bromobenzene so obtained in THF (70 ml) which had been cooled to -78° C. The mixture was stirred at -78° C. for 15 minutes. DMF (4.6 ml) was added and the mixture was allowed to warm to ambient temperature.

The mixture was poured into a saturated aqueous ammonium chloride solution and extracted with diethyl ether.

The organic phase was washed with brine, dried (MgSO4) and evaporated.

The residue was purified by column chromatography using methylene chloride as eluent.

There was thus obtained 4-(2-methyl-1,3-dioxolan-2-yl)benzaldehyde (3.5 g, 60percent) as a liquid.

Patent; Zeneca Limited; Zeneca PHARMA S A; US5332757; (1994); (A) English View in Reaxys

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O O

Br

O O

O

O O– K+

O O

OH

Rx-ID: 3938111 View in Reaxys 135/513 Yield

Conditions & References With potassium bromide, Time= 0.0333333h, Irradiation, Mechanism, Product distribution Owen, David J.; O'Donnell, Jennifer; Schutt, Wendy; Morrow, Jeffrey; Li, Yuzhuo; Journal of Organic Chemistry; vol. 58; nb. 23; (1993); p. 6203 - 6207 View in Reaxys -1

NH 2

F (v4)

F

B FF

O

O

Br

Br

NH 2

N+ N

Rx-ID: 3989186 View in Reaxys 136/513 Yield

Conditions & References

67 %

With copper(II) bis(tetrafluoroborate), sodium bromide in water, acetone, Time= 2.5h, T= 15 - 20 °C Grishchuk, B. D.; Gorbovoi, P. M.; Kudrik, E. Ya.; Ganushchak, N. I.; Russian Journal of General Chemistry; vol. 63; nb.

10.2; (1993); p. 1620 - 1623; Zhurnal Obshchei Khimii; vol. 63; nb. 10; (1993); p. 2335 - 2341 View in Reaxys

Br

HO

Rx-ID: 24366451 View in Reaxys 137/513 Yield

Conditions & References 15.A : Preparation of the t-hydroxy-2 phenyl-1-r-(piperidino-1)-1 cyclohexane of formula: STR37 A) The Grignard reagent resulting from the action of 48.9 g (0.3M) of bromobenzene on 8.75 g (0.35M) of magnesium in the form of turnings is prepared in 300 ml of anhydrous ether.

To it is added 19.6 g (0.2M) of cyclohexanone dissolved in 300 ml of anhydrous ether.

Stirring takes place for 3 h on the reflux condenser and the complex is decomposed by a cold, saturated NH4 Cl solution and then, after settling, the liquids are extracted with ether (3*200 ml).

The ethers are dried (Na2 SO4) and evaporated in vacuo to give a yellowish solid which, after two crystallizations in petroleum ether, give 25 g of white 1-phenyl-cyclohexanol melting at 60° to 61° C. (IR).

Patent; Centre National de La Recherche Scientifique; US5179109; (1993); (A) English View in Reaxys -1 Br+

F F

F (v6)

F

Br

P F

F

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Br

Br

Br

Rx-ID: 2519602 View in Reaxys 138/513 Yield

Conditions & References in acetone, Irradiation, Quantum yield, Product distribution, Mechanism Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1838 - 1844 View in Reaxys -1 Br+

F F

F (v6)

F

Br

N

P F

F

Br Br

H N

O

Br

Rx-ID: 3738454 View in Reaxys 139/513 Yield

Conditions & References Irradiation, Quantum yield, Product distribution, Mechanism Dektar, John L.; Hacker, Nigel P.; Journal of Organic Chemistry; vol. 56; nb. 5; (1991); p. 1838 - 1844 View in Reaxys

F

Br

F

Bi

Br

Bi

Br

F

F

Br

Br

F F

Rx-ID: 26733768 View in Reaxys 140/513 Yield

Conditions & References With bromine in not given, -30°C Pasenok, Sergej; Naumann, Dieter; Tyrra, Wieland; Journal of Organometallic Chemistry; vol. 417; nb. 3; (1991); p. C47 C49 ; (from Gmelin) View in Reaxys

F F

B– FF

(v6) H (v6) H HB B HB (v6)

(v6) (v6) B (v6) H +B

Br (v2)

H B BH (v6) (v6) (v6) (v6)

BH H B BH (v6) H (v6)

(v6)

Br

(v6)

(v6)

(v6) BH(v6) HB BH HB BH (v6) (v6) HB BH B BH F(v6) (v6) (v6) (v6)B H

(v6) H (v6) H HB B BH HB BH (v6) (v6) (v6) (v6) B B H H B H BrB B H (v6) H (v6)

(v6) (v6)(v6)

(v6)

Rx-ID: 26750836 View in Reaxys 141/513 Yield 45 %, 8 %, 10 %

Conditions & References With sodium fluoride in dichloromethane, water, vigorously stirred under reflux for 5 h; GLC, chromatographed, GC-MS Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 1760 - 1765 ; (from Gmelin) View in Reaxys

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F F

B– FF

(v6) H (v6) H HB B HB (v6)

(v6) (v6) B (v6) H +B

H B BH (v6)

BH H B BH (v6) H (v6)

Br (v2)

(v6) H (v6) H HB B BH HB BH (v6) (v6) (v6) (v6) B B H H B H BrB B H (v6) H (v6)

Br

(v6) (v6) (v6)

(v6) H (v6) H HB B BH HB BH (v6) (v6) (v6) (v6) B B H H B H HOB B H (v6) H (v6)

(v6) (v6) (v6)

O N

(v6) (v6) (v6)

O

Rx-ID: 26750837 View in Reaxys 142/513 Yield

Conditions & References

2.5 %, 92 With sodium nitrite in dichloromethane, water, vigorously stirred under reflux for 2.5 h; GLC, chromatographed (silica, 1. hex%, 1 %, 1 % ane, 2. ether) Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 1760 - 1765 ; (from Gmelin) View in Reaxys

F F

B– FF

(v6) H (v6) H HB B HB (v6)

(v6) (v6) B (v6) H +B

H B BH (v6)

Br

(v6) (v6) (v6)

BH H B BH (v6) H (v6)

Br (v2)

(v6) H (v6) H HB B BH HB BH (v6) (v6) (v6) (v6) (v6)(v6)B BH (v6) HB B H Cl B H (v6) H (v6)

Rx-ID: 26750838 View in Reaxys 143/513 Yield

Conditions & References

>99

With sodium chloride in chloroform, water, byproducts: bromobenzene, benzene; vigorously stirred under reflux for 1 h; GLC Grushin, Vladimir V.; Demkina, Iraida I.; Tolstaya, Tat'yana P.; Inorganic Chemistry; vol. 30; (1991); p. 1760 - 1765 ; (from Gmelin) View in Reaxys

N

HO

Br

N

N

Rx-ID: 1975014 View in Reaxys 144/513 Yield

Conditions & References

45 % Chromat., 35 % Chromat.

With hydrogen bromide, Time= 0.5h, Heating, Mechanism Satyamurthy, N.; Barrio, Jorge R.; Schmidt, Derrick G.; Kammerer, Craig; Bida, Gerald T.; Phelps, Michael E.; Journal of Organic Chemistry; vol. 55; nb. 15; (1990); p. 4560 - 4564 View in Reaxys

Cl

Br

Cl

Br

Rx-ID: 1981445 View in Reaxys 145/513 Yield

Conditions & References With sodium tetrahydroborate, 9,10-dihydro-10-methylacridine in water, acetonitrile, T= 24.9 °C , Irradiation, other bromochlorobenzenes and halobenzyl halides; selectivity of the photocatalytic reductive dehalogenation, Product distribution Ishikawa, Masashi; Fukuzumi, Sbunichi; Journal of the American Chemical Society; vol. 112; nb. 24; (1990); p. 8864 - 8870 View in Reaxys

O

H N

N N

N

Br

N

Rx-ID: 3737757 View in Reaxys 146/513

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Yield

Conditions & References

93 % Chromat., 4 % Chromat.

With sulfonic acid resin (H+ form), lithium bromide, Time= 0.5h, Heating, var. of time, var. solvents, var. nucleophiles, var. triazenes, Mechanism Satyamurthy, N.; Barrio, Jorge R.; Schmidt, Derrick G.; Kammerer, Craig; Bida, Gerald T.; Phelps, Michael E.; Journal of Organic Chemistry; vol. 55; nb. 15; (1990); p. 4560 - 4564 View in Reaxys

I

Br

Rx-ID: 1793676 View in Reaxys 147/513 Yield

Conditions & References With copper(I) bromide, Time= 24h, T= 135 °C Couture, Christiane; Paine, Anthony James; Canadian Journal of Chemistry; vol. 63; (1985); p. 111 - 120 View in Reaxys With bromobenzene, tetrabutylammomium bromide, o-CH3C6H4NiBr(PEt3)2 in benzene, Time= 20h, T= 80 °C , sealed tube, Yield given Tsou, T. T.; Kochi, J. K.; Journal of Organic Chemistry; vol. 45; nb. 10; (1980); p. 1930 - 1937 View in Reaxys With aluminum oxide, copper(I) bromide in various solvent(s), Time= 9h, T= 150 °C Clark, James H.; Jones, Craig W.; Duke, Catherine V. A.; Miller, Jack M.; Journal of Chemical Research, Miniprint; nb. 8; (1989); p. 1745 - 1758 View in Reaxys With copper(I) bromide in N,N-dimethyl acetamide, T= 137 °C , equilibrium order; aalso at 53 deg C; also with CuBr2, Equilibrium constant, Rate constant Couture, Christiane; Paine, Anthony James; Canadian Journal of Chemistry; vol. 63; (1985); p. 111 - 120 View in Reaxys

Br–

+Mg

O

O

Br

Rx-ID: 1848126 View in Reaxys 148/513 Yield

Conditions & References With xenon difluoride, Time= 4h, Ambient temperature, Further byproducts given Bregar, Zvonko; Stavber, Stojan; Zupan, Marko; Journal of Fluorine Chemistry; vol. 44; (1989); p. 187 - 194 View in Reaxys

-1 F

F

F

F

F

(v4)

F F F

F

F

B FF

Br

F

Br+

F

F

F

F F F

F

F

F

Rx-ID: 1960747 View in Reaxys 149/513

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Yield

Conditions & References

0.1 g, 20 % Chromat.

With cesium fluoride in various solvent(s), Time= 2h, T= 20 °C German, L. S.; Delyagina, N. I.; Vanchikov, A. N.; Tolstaya, T. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 1.2; (1989); p. 174 - 176; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 38; nb. 1; (1989); p. 188 - 190 View in Reaxys H

H Br

H Br Br

Br

H

H

Br

H

Rx-ID: 2218506 View in Reaxys 150/513 Yield

Conditions & References Time= 1h, T= 130 °C Molchanov, A. P.; Pecheritsyna, Ya. P.; Kostikov, R. R.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 6.1; (1989); p. 1076 - 1081; Zhurnal Organicheskoi Khimii; vol. 25; nb. 6; (1989); p. 1195 - 1200 View in Reaxys

-1

O

F (v4)

F

B FF

Br

HO

Br+

Rx-ID: 2243757 View in Reaxys 151/513 Yield

Conditions & References

60 % Chromat.

With sodium hydroxide in water, Time= 1h, T= 20 °C , other diphenylhalogenonium tetrafluoroborates; other nucleophiles; var. reaction conditions, Product distribution, Mechanism Tolstaya, T. P.; Demkina, I. I.; Grushin, V. V.; Vanchikov, A. N.; Journal of Organic Chemistry USSR (English Translation); vol. 25; nb. 12.2; (1989); p. 2305 - 2310; Zhurnal Organicheskoi Khimii; vol. 25; nb. 12; (1989); p. 2569 - 2576 View in Reaxys -1

F (v4)

B FF

F

Br

Cl

N+ N

Rx-ID: 2287726 View in Reaxys 152/513 Yield

Conditions & References

1.7 %

With sodium bromide, sodium chloride in glycerol, T= 21 - 23.5 °C , investigations of thermal dediazoniation in various solvents as a function of viscosity; the reaction are diffusion controlled, Product distribution, Kinetics Lorand, John P.; Tetrahedron Letters; vol. 30; nb. 52; (1989); p. 7337 - 7340 View in Reaxys

H 14C Br

14C

H 14C

H 14C

14CH 14CH

Li

Li

Br

14CH

14C

H 14C

14CH 14CH 14CH

Rx-ID: 2925302 View in Reaxys 153/513 Yield

Conditions & References in diethyl ether, T= 24.9 °C , effect of alkali metal and tetramethylammonium halides; ΔG(excit.), Rate constant Batalov, A. P.; Russian Journal of Physical Chemistry; vol. 63; nb. 2; (1989); p. 192 - 195; Zhurnal Fizicheskoi Khimii; vol. 63; (1989); p. 354 - 358 View in Reaxys

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in diethyl ether, T= 25 °C , other temperature, ΔH excit., ΔH excit., ΔH excit, Product distribution, Thermodynamic data Batalov, A. P.; Malenova, I. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 3; (1984); p. 613 - 617,542 - 546 View in Reaxys

N HN

Br

Br

Br

N

H 2N

Rx-ID: 3332211 View in Reaxys 154/513 Yield

Conditions & References

85 %

With copper(II) sulfate in water, acetic acid, Time= 1h Varea, Teresa; Gonzalez-Nunez, Maria E.; Rodrigo-Chiner, Javier; Asensio, Gregorio; Tetrahedron Letters; vol. 30; nb. 35; (1989); p. 4709 - 4712 View in Reaxys -1

F

F

F (v4)

F

F

F

F

B FF

F F

Br+

F F

Br

F

O

F

F O F F

Rx-ID: 3421280 View in Reaxys 155/513 Yield

Conditions & References

57 % Chromat.

With cesium fluoride in acetonitrile, Time= 3h, T= 35 °C , Yields of byproduct given German, L. S.; Delyagina, N. I.; Vanchikov, A. N.; Tolstaya, T. P.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 1.2; (1989); p. 174 - 176; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; vol. 38; nb. 1; (1989); p. 188 - 190 View in Reaxys

Cl

Cl N

Br

Cl

Br

HN

Rx-ID: 3861626 View in Reaxys 156/513 Yield

Conditions & References Yield given Smith III, Milton R.; Hillhouse, Gregory L.; Journal of the American Chemical Society; vol. 111; nb. 10; (1989); p. 3764 3765 View in Reaxys

Br

Br Br

Br

Rx-ID: 4032774 View in Reaxys 157/513 Yield 17.9 % Chromat., 36.3 % Chromat.

Conditions & References Time= 20h, T= 25 °C , Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

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Br

Br

Br

Br

Rx-ID: 4032775 View in Reaxys 158/513 Yield

Conditions & References

10.5 % Chromat., 20.0 % Chromat., 8.8 % Chromat.

Time= 20h, T= 25 °C , Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Br

Br Br

Br

Rx-ID: 4032823 View in Reaxys 159/513 Yield

Conditions & References

24.2 % Chromat., 16.0 % Chromat.

Br

Time= 20h, T= 25 °C , Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Br

Br Br

magnesium

Br

Rx-ID: 18137434 View in Reaxys 160/513 Yield

Conditions & References Reaction Steps: 3 1: 1.5 percent Chromat. / 20 h / 25 °C / Irradiation 2: 1.3 percent Chromat. / 24 h / 25 °C / Irradiation 3: 19.6 percent Chromat. / 20 h / 25 °C / Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Br

Br Br

magnesium

Br

Rx-ID: 18141229 View in Reaxys 161/513 Yield

Conditions & References Reaction Steps: 2 1: 1.3 percent Chromat. / 24 h / 25 °C / Irradiation 2: 19.6 percent Chromat. / 20 h / 25 °C / Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

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Br

Br Br

Br

magnesium

Br

Rx-ID: 18141330 View in Reaxys 162/513 Yield

Conditions & References Reaction Steps: 3 1: 11.7 percent Chromat. / 20 h / 25 °C / Irradiation 2: 1.3 percent Chromat. / 24 h / 25 °C / Irradiation 3: 19.6 percent Chromat. / 20 h / 25 °C / Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Br Br

magnesium

Br Br

Rx-ID: 18141939 View in Reaxys 163/513 Yield

Conditions & References Reaction Steps: 2 1: 9.5 percent Chromat. / 24 h / 25 °C / Irradiation 2: 9.9 percent Chromat. / 20 h / 25 °C / Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Br

sulfur dioxide

magnesium

Rx-ID: 18176781 View in Reaxys 164/513 Yield

Conditions & References Reaction Steps: 4 1: 19.7 percent Chromat. / 20 h / 25 °C / Irradiation 2: 1.5 percent Chromat. / 20 h / 25 °C / Irradiation 3: 1.3 percent Chromat. / 24 h / 25 °C / Irradiation 4: 19.6 percent Chromat. / 20 h / 25 °C / Irradiation Nakada; Miura; Nishiyama; Higashi; Mori; Hirota; Ishii; Bulletin of the Chemical Society of Japan; vol. 62; nb. 10; (1989); p. 3122 - 3126 View in Reaxys

Br

O

Cl

O

O

O

O

HO

HO

Br

Br

HO

Cl

Rx-ID: 1620671 View in Reaxys 165/513 Yield

Conditions & References With tetrabutylammomium bromide in N,N-dimethyl-formamide, T= 5 °C , electrolysis (I=0.4 A), Yield given. Further byproducts given. Yields of byproduct given

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Heintz, Monique; Sock, Oumar; Saboureau, Christophe; Perichon, Jacques; Troupel, Michel; Tetrahedron; vol. 44; nb. 6; (1988); p. 1631 - 1636 View in Reaxys F

F

F

O

I

Na +

F

F

Br

F

O–

Rx-ID: 1793315 View in Reaxys 166/513 Yield

Conditions & References

45 % Chromat.

With 1-methyl-pyrrolidin-2-one, copper(I) bromide, Time= 4h, T= 160 °C , examination of the oxidation state of copper, further reagents and their quantities, further arenes and sodium perfluoroalkane carboxylates, temperature; experiments with (14)C, Product distribution, Mechanism Carr, Gillian E.; Chambers, Richard D.; Holmes, Thomas F.; Parker, David G.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 921 - 926 View in Reaxys

Cl

Cl

N N

Br

O

(v1)

N

Cl HO

Cl

Cl

Cl

O

Cl N

Br

N

Cl

O

Cl

O

Rx-ID: 1911589 View in Reaxys 167/513 Yield

Conditions & References T= 80 °C , different reactant concentrations, with and without C6F6 investigated, Rate constant, Product distribution Mathew, Lukose; Warkentin, John; Canadian Journal of Chemistry; vol. 66; (1988); p. 11 - 16 View in Reaxys

O

O

O

O

Mg

Br

Br

Mg

O O

O

O

Rx-ID: 2425822 View in Reaxys 168/513 Yield

Conditions & References in diethyl ether, toluene, Time= 24h, T= 25 °C , Yield given Markies, Peter R.; Nomoto, Tateo; Akkerman, Otto S.; Bickelhaupt, Friedrich; Smeets, Wilberth J. J.; Spek, Anthony L.; Angewandte Chemie; vol. 100; nb. 8; (1988); p. 1143 - 1144 View in Reaxys

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N

N

N Si

N

N

N

Br

N

N

Rx-ID: 3726849 View in Reaxys 169/513 Yield

Conditions & References With copper(ll) bromide in tetrahydrofuran, Time= 7h, T= 50 °C , Product distribution, Mechanism Tamao, Kohei; Akita, Munetaka; Kato, Hidehito; Kumada, Makoto; Journal of Organometallic Chemistry; vol. 341; (1988); p. 165 - 180 View in Reaxys With bromine in diethyl ether, Time= 5h, Product distribution, Mechanism Tamao, Kohei; Akita, Munetaka; Kato, Hidehito; Kumada, Makoto; Journal of Organometallic Chemistry; vol. 341; (1988); p. 165 - 180 View in Reaxys With N-Bromosuccinimide in benzene, Time= 7.5h, Ambient temperature, variation of solvents and reaction conditions, Product distribution, Mechanism Tamao, Kohei; Akita, Munetaka; Kato, Hidehito; Kumada, Makoto; Journal of Organometallic Chemistry; vol. 341; (1988); p. 165 - 180 View in Reaxys

Br

O

O O

O

N H

O

O

O

O Br

O

NH

O

O

O

Rx-ID: 4033641 View in Reaxys 170/513 Yield 64 %

Conditions & References in toluene, Time= 7h, T= 85 °C Baldwin, Jack S.; Adlington, Robert M.; Lowe, Christopher; O'Neil, Ian A.; Sanders, Gillian L.; et al.; Journal of the Chemical Society, Chemical Communications; nb. 15; (1988); p. 1030 - 1031 View in Reaxys

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Cl

Br

Rx-ID: 4269828 View in Reaxys 171/513 Yield

Conditions & References With bromine in gaseous matrix, T= 40 °C , collision energy E(c), Thermodynamic data Robinson, Gary N.; Continetti, Robert E.; Lee, Yuan T.; Journal of Chemical Physics; vol. 89; nb. 10; (1988); p. 6226 - 6237 View in Reaxys

O

Br

N

C6H4Br2

O

Rx-ID: 6726728 View in Reaxys 172/513 Yield

Conditions & References With potassium bromide, sodium nitrite in water, trifluoroacetic acid, Time= 0.25h, T= 20 °C , under argon, other reagent, other time, Product distribution Cheprakov, A. V.; Makhon'kov, D. I.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 24; nb. 2; (1988); p. 217 - 223; Zhurnal Organicheskoi Khimii; vol. 24; nb. 2; (1988); p. 248 - 255 View in Reaxys

Br

N Br

N

Br

Rx-ID: 1496416 View in Reaxys 173/513 Yield

Conditions & References

21 % Chromat., 22 % Chromat.

21 % Chromat., 22 % Chromat.

With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, T= 40 °C , electroreduction: Pt electrode vs. Ag/Ag+ Egashira, Naoyoshi; Takenga, Jun; Hori, Fumikai; Bulletin of the Chemical Society of Japan; vol. 60; nb. 7; (1987); p. 2671 2673 View in Reaxys With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, T= 40 °C , electroreduction: electrode Pt vs. Ag/Ag+; different electrodes, benzyne acceptors and substrates, Product distribution Egashira, Naoyoshi; Takenga, Jun; Hori, Fumikai; Bulletin of the Chemical Society of Japan; vol. 60; nb. 7; (1987); p. 2671 2673 View in Reaxys

Br

N

Br Br

N O

O

Rx-ID: 1500335 View in Reaxys 174/513 Yield 12 % Chromat., 22 % Chromat.

Conditions & References With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, T= 40 °C , electroreduction: Pt electrode vs. Ag/Ag+ Egashira, Naoyoshi; Takenga, Jun; Hori, Fumikai; Bulletin of the Chemical Society of Japan; vol. 60; nb. 7; (1987); p. 2671 2673 View in Reaxys

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OH

Br

Br

N

N

Br

Rx-ID: 1506919 View in Reaxys 175/513 Yield

Conditions & References

14 % Chromat., 36 % Chromat.

With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, T= 40 °C , electroreduction: Pt electrode vs. Ag/Ag+ Egashira, Naoyoshi; Takenga, Jun; Hori, Fumikai; Bulletin of the Chemical Society of Japan; vol. 60; nb. 7; (1987); p. 2671 2673 View in Reaxys

Br

N Br

N

Br

Rx-ID: 1555526 View in Reaxys 176/513 Yield

Conditions & References

11 % Chromat., 45 % Chromat.

With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, T= 40 °C , electroreduction: Pt electrode vs. Ag/Ag+ Egashira, Naoyoshi; Takenga, Jun; Hori, Fumikai; Bulletin of the Chemical Society of Japan; vol. 60; nb. 7; (1987); p. 2671 2673 View in Reaxys

H

H

Br

Br

Br

Br

Br

Br

H Br

Br

H

H

Rx-ID: 2028180 View in Reaxys 177/513 Yield

Conditions & References

4 %, 34 %, 35 %

With N-bromobis(trimethylsilyl)amine, T= 75 °C , different reagent and temperature, Product distribution Walton, John C.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1987); p. 1252 - 1254 View in Reaxys

H

Br

Br

H Br

Br

H

H

H

Rx-ID: 2028181 View in Reaxys 178/513 Yield 4 %, 34 %, 35 %

Conditions & References With N-bromobis(trimethylsilyl)amine, T= 75 °C , Further byproducts given Walton, John C.; Journal of the Chemical Society, Chemical Communications; nb. 16; (1987); p. 1252 - 1254

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View in Reaxys -1 F (v4)

B FF

F

Br Br

N+

Cl

Br

Br

F

N

Rx-ID: 2327227 View in Reaxys 179/513 Yield

Conditions & References

11.1 % With 18-crown-6 ether, 1,2-dichloro-ethane, T= 50 °C , Rate constant Chromat., 6.6 % Chro- Nakazumi, Hiroyuki; Kitao, Teijiro; Zollinger, Heinrich; Journal of Organic Chemistry; vol. 52; nb. 13; (1987); p. 2825 2830 mat.

View in Reaxys

Br

N

N

Br Br

Rx-ID: 3311258 View in Reaxys 180/513 Yield 13 % Chromat., 25 % Chromat.

H 2N

Conditions & References With tetrabutylammonium perchlorate in N,N-dimethyl-formamide, T= 40 °C , electroreduction: Pt electrode vs. Ag/Ag+ Egashira, Naoyoshi; Takenga, Jun; Hori, Fumikai; Bulletin of the Chemical Society of Japan; vol. 60; nb. 7; (1987); p. 2671 2673 View in Reaxys

Br

Cl

Rx-ID: 3377170 View in Reaxys 181/513 Yield

Conditions & References With copper(I) bromide, hydrogenchloride, sodium nitrite, 1.) water, poly(ethylene glycol), CH2Cl2, 0 deg C; 2.) poly(ethylene glycol), CH2Cl2, from 0 deg C to RT, Yield given. Multistep reaction. Yields of byproduct given Suzuki, Nobutaka; Azuma, Terukazu; Kaneko, Yoshihiro; Izawa, Yasuji; Tomioka, Hideo; Nomoto, Tateo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 645 - 648 View in Reaxys

Br–

+Mg

Br

Mg

Br

Br

Rx-ID: 3399905 View in Reaxys 182/513 Yield 66 (unit not given), 8 (unit not given)

Conditions & References in tetrahydrofuran, diethyl ether, Time= 0.166667h, T= 20 °C , Product distribution Bumagin, N. A.; Ponomarev, A. B.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol. 23; nb.

7; (1987); p. 1222 - 1231; Zhurnal Organicheskoi Khimii; vol. 23; nb. 7; (1987); p. 1354 - 1364 View in Reaxys

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Si

Si

Br

O

O Si

O

Si

Si

Si

O

Br

Si Si

Si

Si

Rx-ID: 3723743 View in Reaxys 183/513 Yield

Conditions & References

83 %

With bromine, iron in tetrachloromethane, Time= 1h, Heating Pillmann, Simone; Klingebiel, Uwe; Journal of Organometallic Chemistry; vol. 323; (1987); p. 1 - 10 View in Reaxys

Br–

Br

+Mg

Br

Rx-ID: 5802744 View in Reaxys 184/513 Yield

Conditions & References

82 %, 7 %

With copper(l) iodide, nitrobenzene in tetrahydrofuran, -8 deg C, 1 hr.; r.t. 30 min.; reflux 30 min.

Rahman, Mohammed T.; Nahar, Syeda K.; Journal of Organometallic Chemistry; vol. 329; nb. 1; (1987); p. 133 - 138 View in Reaxys With copper(l) iodide, nitrobenzene in tetrahydrofuran, -8 deg C, 1 hr.; r.t. 30 min; reflux 30 min., Product distribution Rahman, Mohammed T.; Nahar, Syeda K.; Journal of Organometallic Chemistry; vol. 329; nb. 1; (1987); p. 133 - 138 View in Reaxys

F Si Si

Si

Br

copper bromide

F Si

Rx-ID: 18319301 View in Reaxys 185/513 Yield

Conditions & References Reaction Steps: 3 1: 82 percent / tetrahydrofuran / 3 h / Heating 2: 35 percent / KOH / H2O / 1 h / 120 °C 3: Br2, Fe / CCl4 / 1 h / Heating With potassium hydroxide, bromine, iron in tetrahydrofuran, tetrachloromethane, water Pillmann, Simone; Klingebiel, Uwe; Journal of Organometallic Chemistry; vol. 323; (1987); p. 1 - 10 View in Reaxys Reaction Steps: 4 1: KOH / H2O / 80 - 100 °C 2: 85 percent / MeLi / tetrahydrofuran / 2 h / Heating 3: 35 percent / KOH / H2O / 1 h / 120 °C 4: Br2, Fe / CCl4 / 1 h / Heating With potassium hydroxide, methyllithium, bromine, iron in tetrahydrofuran, tetrachloromethane, water Pillmann, Simone; Klingebiel, Uwe; Journal of Organometallic Chemistry; vol. 323; (1987); p. 1 - 10 View in Reaxys Reaction Steps: 4 1: KOH / H2O / 80 - 100 °C 2: KOH / H2O

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3: 85 percent / n-C4H9Li / hexane; tetrahydrofuran / 2 h / Heating 4: Br2, Fe / CCl4 / 1 h / Heating With potassium hydroxide, n-butyllithium, bromine, iron in tetrahydrofuran, tetrachloromethane, hexane, water Pillmann, Simone; Klingebiel, Uwe; Journal of Organometallic Chemistry; vol. 323; (1987); p. 1 - 10 View in Reaxys

Si O

F Si

Br

copper bromide

Si

Si

Rx-ID: 18322382 View in Reaxys 186/513 Yield

Conditions & References Reaction Steps: 3 1: 85 percent / MeLi / tetrahydrofuran / 2 h / Heating 2: 35 percent / KOH / H2O / 1 h / 120 °C 3: Br2, Fe / CCl4 / 1 h / Heating With potassium hydroxide, methyllithium, bromine, iron in tetrahydrofuran, tetrachloromethane, water Pillmann, Simone; Klingebiel, Uwe; Journal of Organometallic Chemistry; vol. 323; (1987); p. 1 - 10 View in Reaxys Reaction Steps: 3 1: KOH / H2O 2: 85 percent / n-C4H9Li / hexane; tetrahydrofuran / 2 h / Heating 3: Br2, Fe / CCl4 / 1 h / Heating With potassium hydroxide, n-butyllithium, bromine, iron in tetrahydrofuran, tetrachloromethane, hexane, water Pillmann, Simone; Klingebiel, Uwe; Journal of Organometallic Chemistry; vol. 323; (1987); p. 1 - 10 View in Reaxys

Si O

HO Si

Br

Si

copper bromide

Si

Rx-ID: 18322388 View in Reaxys 187/513 Yield

Conditions & References Reaction Steps: 2 1: 85 percent / n-C4H9Li / hexane; tetrahydrofuran / 2 h / Heating 2: Br2, Fe / CCl4 / 1 h / Heating With n-butyllithium, bromine, iron in tetrahydrofuran, tetrachloromethane, hexane Pillmann, Simone; Klingebiel, Uwe; Journal of Organometallic Chemistry; vol. 323; (1987); p. 1 - 10 View in Reaxys

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Si Br

Si

Si Si

copper bromide

F

O Si

Rx-ID: 18329668 View in Reaxys 188/513 Yield

Conditions & References Reaction Steps: 2 1: 35 percent / KOH / H2O / 1 h / 120 °C 2: Br2, Fe / CCl4 / 1 h / Heating With potassium hydroxide, bromine, iron in tetrachloromethane, water Pillmann, Simone; Klingebiel, Uwe; Journal of Organometallic Chemistry; vol. 323; (1987); p. 1 - 10 View in Reaxys

C

O

I

Br

Br

Br

O

Rx-ID: 2011185 View in Reaxys 189/513 Yield 70 %, 4 % Chromat.

Conditions & References With tri-n-butyl-tin hydride, tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, T= 50 °C , p= 2280Torr Baillargeon, Victor P.; Stille, J. K.; Journal of the American Chemical Society; vol. 105; nb. 24; (1983); p. 7175 - 7176 View in Reaxys

70 %, 10 %

With tri-n-butyl-tin hydride, tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran, T= 50 °C , p= 2280Torr Baillargeon,V.P.; Stille,J.K.; Journal of the American Chemical Society; vol. 108; (1986); p. 452 View in Reaxys

As Br

Br As Br

Rx-ID: 2184571 View in Reaxys 190/513 Yield

Conditions & References With bromine in acetonitrile, Time= 0.5h, T= 0 °C Raizada, Meenu Singh; Nigam, H. L.; Journal of the Indian Chemical Society; vol. 63; (1986); p. 722 - 724 View in Reaxys

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Br As

Br As

Br

(v7)

Br Br

Rx-ID: 2184572 View in Reaxys 191/513 Yield

Conditions & References With bromine in acetonitrile, Time= 0.5h, T= 0 °C Raizada, Meenu Singh; Nigam, H. L.; Journal of the Indian Chemical Society; vol. 63; (1986); p. 722 - 724 View in Reaxys

Li

Br

Rx-ID: 2926765 View in Reaxys 192/513 Yield

Conditions & References With Cl(CF2)4SO2Br in diethyl ether, T= 10 °C Huang, Wei-Yuan; Chen, Jian-Long; Hu, Li-Qing; Bulletin de la Societe Chimique de France; nb. 6; (1986); p. 881 - 884 View in Reaxys

O

O N N

Br

N

Br

Br

H N

H N

Br

N

Br

N

N

N

Br

Br Br Br

N

N

Br

N

O

Br

Br Br

O

O

N

Br O

Rx-ID: 3918380 View in Reaxys 193/513 Yield

Conditions & References in benzene, Time= 3h, Heating, other bromo-1-nitro-1H-pyrazoles; var. solvents, temp., time and reagents, Product distribution, Mechanism Juffermans, J. P. H.; Habraken, Clarisse L.; Journal of Organic Chemistry; vol. 51; nb. 24; (1986); p. 4656 - 4660 View in Reaxys Ni(mes)(Ph)(PMe2Ph)2

Br

Br

Rx-ID: 7066213 View in Reaxys 194/513 Yield

Conditions & References With bromine in diethyl ether, Time= 0.5h, Ambient temperature, Yield given

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Coronas, Juan M.; Muller, Guillermo; Rocamora, Mercedes; Journal of Organometallic Chemistry; vol. 301; (1986); p. 227 236 View in Reaxys

Br

Ni(o-tol)Ph(PEt3)2

Br

Rx-ID: 7244092 View in Reaxys 195/513 Yield

Conditions & References With bromine in diethyl ether, Time= 0.5h, Ambient temperature, Yield given Coronas, Juan M.; Muller, Guillermo; Rocamora, Mercedes; Journal of Organometallic Chemistry; vol. 301; (1986); p. 227 236 View in Reaxys Br (v2)

Cl Cl

Hg

Br Br

Cl

Cl

Br

Br

Br

Br

Cl

Br

Br

Cl

Cl

Br

Br

Br

Cl

Br

Br

Br

Br

Br

Rx-ID: 1782573 View in Reaxys 196/513 Yield

Conditions & References in benzene, Time= 24h, T= 70 °C , var. solvents, var. additives, Product distribution, Mechanism Lambert, Joseph B.; Boch, Richard J.; Larson, Eric G.; Journal of Organic Chemistry; vol. 50; nb. 17; (1985); p. 3054 - 3059 View in Reaxys O

O

S

Br

Br

HO

Rx-ID: 2105356 View in Reaxys 197/513 Yield

Conditions & References With sulfuric acid, Time= 27.7778h, T= 150 °C , sealed tube, various H2SO4 concentration, Kinetics, Rate constant Krylov E. N.; Pelevina, M. B.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1983 1987; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2166 - 2171 View in Reaxys With phosphoric acid, T= 150 °C , various H3PO4 concentration, Rate constant Krylov E. N.; Radzyun, O. S.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1987 1991; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2171 - 2176 View in Reaxys With perchloric acid, T= 150 °C , other concentration of HClO4, Rate constant Krylov, E. N.; Mironova, O. A.; Journal of Organic Chemistry USSR (English Translation); vol. 21; (1985); p. 1901 - 1904; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2077 - 2081 View in Reaxys

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F

F

F

F

F

F

F F

O

F

F

F

O

O –Si

N+

Br

F

F Si

F

O

F

F

F

F

F

F

F

F

F F

Rx-ID: 2641099 View in Reaxys 198/513 Yield

Conditions & References

75 %

With bromine, Time= 24h, T= 25 °C Stevenson, William H.; Wilson, Scott; Martin, J. C.; Farnham, William B.; Journal of the American Chemical Society; vol.

107; nb. 22; (1985); p. 6340 - 6352 View in Reaxys

O

O O

O O

Br

Bi

Rx-ID: 2697740 View in Reaxys 199/513 Yield

Conditions & References With copper diacetate, calcium bromide in isopropyl alcohol, Time= 80h, T= 20 °C , Yield given. Yields of byproduct given Dodonov, V. A.; Gushin, A. V.; Brilkina, T. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 11; (1985); p. 2514 2519,2232 - 2236 View in Reaxys

Bi

Br

Br

Rx-ID: 2831724 View in Reaxys 200/513 Yield 70 %

Conditions & References With bromine in tetrahydrofuran, T= -70 - 0 °C , Product distribution Steinseifer, Fritz; Kauffmann, Thomas; Angewandte Chemie; vol. 92; nb. 9; (1980); p. 746 - 747 View in Reaxys

70 % Chromat.

With bromine in diethyl ether, -70 deg C to r.t.

Kauffmann, Thomas; Steinseifer, Fritz; Chemische Berichte; vol. 118; nb. 3; (1985); p. 1031 - 1038 View in Reaxys

Br

SH

Br

Rx-ID: 2939317 View in Reaxys 201/513 Yield

Conditions & References With dicobalt octacarbonyl in water, benzene, T= 185 - 190 °C , p= 46543.3Torr

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Shim, Sang Chul; Antebi, Shlomo; Alper, Howard; Tetrahedron Letters; vol. 26; nb. 16; (1985); p. 1935 - 1938 View in Reaxys

Br

Bi

Br

Rx-ID: 3476964 View in Reaxys 202/513 Yield 67 % Chromat.

Conditions & References With bromine in dichloromethane, -70 deg C to r.t.

Kauffmann, Thomas; Steinseifer, Fritz; Chemische Berichte; vol. 118; nb. 3; (1985); p. 1031 - 1038 View in Reaxys

Bi Br

Br

Rx-ID: 3477234 View in Reaxys 203/513 Yield 86 % Chromat.

Conditions & References With bromine in dichloromethane, -70 deg C to r.t.

Kauffmann, Thomas; Steinseifer, Fritz; Chemische Berichte; vol. 118; nb. 3; (1985); p. 1031 - 1038 View in Reaxys

Bi

Br

Br

Rx-ID: 3477895 View in Reaxys 204/513 Yield 62 % Chromat.

Conditions & References With bromine in dichloromethane, -70 deg C to r.t.

Kauffmann, Thomas; Steinseifer, Fritz; Chemische Berichte; vol. 118; nb. 3; (1985); p. 1031 - 1038 View in Reaxys

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F F

F

F F F

F F

O

O

–Si

N+

F

F

O Br

F Si

F

O

F

F F

F

F F

F F F F F

F

Rx-ID: 3496371 View in Reaxys 205/513 Yield

Conditions & References

74.6 %

With bromine, Time= 24h, T= 25 °C Stevenson, William H.; Wilson, Scott; Martin, J. C.; Farnham, William B.; Journal of the American Chemical Society; vol.

107; nb. 22; (1985); p. 6340 - 6352 View in Reaxys F

F

F

F

F

F O –Si

Li+

Br

radioactive bromine

O F F F

F

F F

Rx-ID: 19279327 View in Reaxys 206/513 Yield

Conditions & References Reaction Steps: 4 1: 59.6 percent / CH2Cl2 2: 72 percent / Br2 / 24 h / 25 °C 3: 95.7 percent / diethyl ether; CH2Cl2 / 1.) -78 deg C, 30 min.; 2.) 25 deg C, 1 h 4: Br2 / 24 h / 25 °C With bromine in diethyl ether, dichloromethane Stevenson, William H.; Wilson, Scott; Martin, J. C.; Farnham, William B.; Journal of the American Chemical Society; vol.

107; nb. 22; (1985); p. 6340 - 6352 View in Reaxys F

F

F

F

F

F O

N+

–Si

Br

radioactive bromine

O F F F

F

F F

Rx-ID: 19279344 View in Reaxys 207/513 Yield

Conditions & References Reaction Steps: 3 1: 75 percent / Br2 / 24 h / 25 °C 2: 95.7 percent / diethyl ether; CH2Cl2 / 1.) -78 deg C, 30 min.; 2.) 25 deg C, 1 h 3: Br2 / 24 h / 25 °C With bromine in diethyl ether, dichloromethane

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Stevenson, William H.; Wilson, Scott; Martin, J. C.; Farnham, William B.; Journal of the American Chemical Society; vol.

107; nb. 22; (1985); p. 6340 - 6352 View in Reaxys F F

F

F

F F

O –Si

N+

Br

radioactive bromine

O

F F F F F

F

Rx-ID: 19304494 View in Reaxys 208/513 Yield

Conditions & References Reaction Steps: 3 1: 75 percent / Br2 / 24 h / 25 °C 2: 95.7 percent / diethyl ether; CH2Cl2 / 1.) -78 deg C, 30 min.; 2.) 25 deg C, 1 h 3: Br2 / 24 h / 25 °C With bromine in diethyl ether, dichloromethane Stevenson, William H.; Wilson, Scott; Martin, J. C.; Farnham, William B.; Journal of the American Chemical Society; vol.

107; nb. 22; (1985); p. 6340 - 6352 View in Reaxys

F F

F

F F

F

F

O

O

F

Br

Si

F

radioactive bromine

F

F F

Rx-ID: 19306286 View in Reaxys 209/513 Yield

Conditions & References Reaction Steps: 2 1: 95.7 percent / diethyl ether; CH2Cl2 / 1.) -78 deg C, 30 min.; 2.) 25 deg C, 1 h 2: Br2 / 24 h / 25 °C With bromine in diethyl ether, dichloromethane Stevenson, William H.; Wilson, Scott; Martin, J. C.; Farnham, William B.; Journal of the American Chemical Society; vol.

107; nb. 22; (1985); p. 6340 - 6352 View in Reaxys Br (v2)

Cl Cl

Hg

Br Br

Cl

Br

Br

Br

Br

Br

Br

Cl

Br

Br

Cl

Br

Cl

Br

Br Br

Rx-ID: 1782574 View in Reaxys 210/513 Yield 0.35 mol, 0.17 mol,

Conditions & References in benzene, Time= 24h, T= 60 °C , effect of temperature, molar ratio, Mechanism, Product distribution

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0.76 mol, 2.69 mol

Lambert; Bosch; Mueller; Kobayashi; Journal of the American Chemical Society; vol. 106; nb. 12; (1984); p. 3584 - 3589 View in Reaxys -1 F (v4)

C

O

F

B FF

Br

Br N+

Br

N

O

Rx-ID: 2002677 View in Reaxys 211/513 Yield

Conditions & References

86 %

With palladium diacetate, polymethylhydrosiloxane in diethyl ether, acetonitrile, Time= 4h, p= 7355.08Torr Kikukawa, Kiyoshi; Totoki, Takatoshi; Wada, Fumio; Matsuda, Tsutomu; Journal of Organometallic Chemistry; vol. 270; nb. 3; (1984); p. 283 - 288 View in Reaxys -1

F

S

(v4)

F

B FF

S– Na +

N

Br

N

N

S

Br+

Rx-ID: 2243750 View in Reaxys 212/513 Yield

Conditions & References in water, 1,2-dichloro-ethane, Time= 0.5h, T= 72 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys -1

F

O

(v4)

F

B FF

S–

Na +

O

Br+

O

O S

O S

Br

HO

O

Rx-ID: 2243751 View in Reaxys 213/513 Yield 77 %

Conditions & References in chloroform, water, Time= 7h, T= 20 °C Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys in chloroform, water, Time= 7h, T= 20 °C , Yields of byproduct given Grushin, V.V.; Kantor, M.M.; Tolstaya, T.P.; Shcherbina, T.M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 10; (1984); p. 2130 - 2135; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 10; (1984); p. 2332 - 2338 View in Reaxys

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O Ag+

O Br

O Br

O–

O

O

Rx-ID: 3918429 View in Reaxys 214/513 Yield

Conditions & References

10 %

T= 25 °C , Product distribution Bryce-Smith, Derek; Isaacs, Neil S.; Tumi, Seddeg O.; Chemistry Letters; (1984); p. 1471 - 1472 View in Reaxys

Br

Br

Br Br

Br

Br

Br

Br

Br

Br

Br

Br

HBr

Br

Rx-ID: 6728594 View in Reaxys 215/513 Yield

Conditions & References With bromine, Time= 16h, T= 55 °C , Irradiation, temperature, Product distribution Bolton, Roger; Bhangar, Muhammad Iqbal; Williams, Gareth H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1984); p. 893 - 896 View in Reaxys

Br

Br Br

Br

Br Br

HBr Br

Br

Rx-ID: 7076880 View in Reaxys 216/513 Yield

Conditions & References With bromine, Time= 20h, T= 50 °C , Irradiation, other time, reagents ratio, Product distribution Bolton, Roger; Bhangar, Muhammad Iqbal; Williams, Gareth H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1984); p. 893 - 896 View in Reaxys Br

Br

Br

Br Br

Br

Br

Br

Br

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81/149

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Br

Br

Br

HBr Br

Br

Rx-ID: 7454305 View in Reaxys 217/513 Yield

Conditions & References Time= 16h, T= 55 °C , Irradiation, other solvents, Product distribution Bolton, Roger; Bhangar, Muhammad Iqbal; Williams, Gareth H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1984); p. 893 - 896 View in Reaxys O O

N

NH N

N Br

N

O N

O N

Br

O Br

O

NH N N

N

O N

N

O

O

Br

N

O

N

N O

NO2, Br2

N O

O N

O

O

O

Rx-ID: 8427402 View in Reaxys 218/513 Yield

Conditions & References

23 %, 27 %, Time= 96h, Heating, Product distribution, Mechanism 7 %, 19 % Zibuck, Regina; Stahl, Mark A.; Barchiesi, Bobbi; Waalwijk, Peter S.; Cohen-Fernandes, Pauline; Habraken, Clarisse L.; Journal of Organic Chemistry; vol. 49; nb. 18; (1984); p. 3310 - 3314 View in Reaxys O O N O

O

O

N

N

NH

O

N Br

N

N

Br

Br

O O

N

O N O

NH

O N O

N

N

N

NO2, Br2

N N

N N Br

O

O

O

O

Rx-ID: 8427403 View in Reaxys 219/513 Yield

Conditions & References

34 %, 26 %, Time= 96h, Heating, Product distribution, Mechanism 10 %, 39 % Zibuck, Regina; Stahl, Mark A.; Barchiesi, Bobbi; Waalwijk, Peter S.; Cohen-Fernandes, Pauline; Habraken, Clarisse L.; Journal of Organic Chemistry; vol. 49; nb. 18; (1984); p. 3310 - 3314

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View in Reaxys I+ Br–

HO

I

Br

O

Rx-ID: 1585275 View in Reaxys 220/513 Yield

Conditions & References

93 % Chromat., 62 % Chromat.

With Copper(I); benzoate, Time= 2.08333h, T= 23 °C , various reaction conditions, Product distribution, Mechanism Lockhart, Thomas P.; Journal of the American Chemical Society; vol. 105; nb. 7; (1983); p. 1940 - 1946 View in Reaxys

Br

HO

Br

O

O Br

Br

Rx-ID: 1900693 View in Reaxys 221/513 Yield

Conditions & References

85.5 %

With potassium hydroxide, PEG-6000, Time= 6h, T= 150 °C Neumann, R.; Sasson, Y.; Tetrahedron; vol. 39; nb. 20; (1983); p. 3437 - 3440 View in Reaxys

Br

Br

Br

Br

Br

Br

Br

Br

Rx-ID: 1903133 View in Reaxys 222/513 Yield

Conditions & References With sodium hydroxide, N-benzyl-N,N,N-triethylammonium chloride in ethanol, dichloromethane, Time= 12h, T= 40 - 50 °C , Ratio of diene and dibromocarbene from 1:4 or 1:6., Product distribution Slobodin, Ya. M.; Ashkinazi, L. A.; Shustareva, T. K.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb.

10; (1983); p. 1787 - 1789; Zhurnal Organicheskoi Khimii; vol. 19; nb. 10; (1983); p. 2062 - 2064 View in Reaxys -1 F (v4)

F

B FF

Br Br

N+

2H

Br

N

Rx-ID: 2327218 View in Reaxys 223/513 Yield

Conditions & References With d(4)-methanol, N-benzyl-1,4-dihydronicotinamide in methanol, Time= 0.166667h, Ambient temperature, with O2 : other D/H ratio, Mechanism Yasui, Shinro; Nakamura, Kaoru; Ohno, Atsuyoshi; Tetrahedron Letters; vol. 24; nb. 32; (1983); p. 3331 - 3334 View in Reaxys

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OH

HO O

O O

O

Br

HO O

Br

P O

O

O

O

Rx-ID: 2823828 View in Reaxys 224/513 Yield

Conditions & References

35 %

With benzyl-triphenoxy-phosphonium; bromide in tetrahydrofuran, Time= 3h, Ambient temperature Eggerer, Hermann; Giesemann, Walter; Aigner, Horst; Liebigs Annalen der Chemie; nb. 9; (1983); p. 1551 - 1560 View in Reaxys

O Br

HO

Rx-ID: 3552589 View in Reaxys 225/513 Yield

Conditions & References With bromine, mercury(II) oxide in nitrobenzene, Time= 2h, T= 180 - 185 °C Uemura, Sakae; Tanaka, Sakuya; Okano, Masaya; Hamana, Masatomo; Journal of Organic Chemistry; vol. 48; nb. 19; (1983); p. 3297 - 3301 View in Reaxys

O

N O

S

Br

N

Br

O

O S

O O S

S

Cl

O O

S Cl

Rx-ID: 3879977 View in Reaxys 226/513 Yield 56 %, 6 %

Conditions & References in tetrachloromethane, Time= 30h, Heating, Product distribution Correa, Carlos M. M. da Silva; Oliveira, Maria Augusta B. C. S.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 711 - 716

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View in Reaxys Br

Cl Cl

Br

Cl

Si

Si Br

Cl

Si

Br

Br Br

Br

Cl

Br

Cl

Cl Si

Br

Br

Br

Rx-ID: 26483922 View in Reaxys 227/513 Yield

Conditions & References in gas, High Pressure; reagents added to tube in dry ice bath, sealed in amts. to develop about 30-50 atm of pressure at 300°C, heated at 350°C for 65 h; analyzed by GLC Scaduto, Patricia M.; Speier, John L.; Inorganic Chemistry; vol. 22; (1983); p. 3363 - 3364 ; (from Gmelin) View in Reaxys

Br

O

N N

N N

N

Br

N

O

Br

Rx-ID: 2210882 View in Reaxys 228/513 Yield

Conditions & References With isopropyl alcohol, thermolysis, Product distribution, Mechanism Mackay, Donald; McIntyre, Deane Douglas; Canadian Journal of Chemistry; vol. 60; (1982); p. 990 - 999 View in Reaxys

Br

O

N N

N N

N N

O

Br

Br

Br

Br

Br

I

Rx-ID: 2210883 View in Reaxys 229/513 Yield

Conditions & References With thermolysis, Product distribution, Mechanism Mackay, Donald; McIntyre, Deane Douglas; Canadian Journal of Chemistry; vol. 60; (1982); p. 990 - 999 View in Reaxys

I+ –O

Br I–

Na +

Br

O

O

Br

I I

Br

Rx-ID: 2281808 View in Reaxys 230/513 Yield

Conditions & References in water, T= 60 °C , relative rates of decomposition of the 9-I-2 intermediate, Product distribution, Mechanism Tanner, Dennis D.; Reed, Darwin W.; Setiloane, B.P.; Journal of the American Chemical Society; vol. 104; nb. 14; (1982); p.

3917 - 3923

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View in Reaxys

I+ –O

Br–

Na +

Br

Br

O

O

I

I

Br

Br

Rx-ID: 2281810 View in Reaxys 231/513 Yield

Conditions & References in water, T= 60 °C , relative rates of decomposition of the 9-I-2 intermediate, Product distribution, Mechanism Tanner, Dennis D.; Reed, Darwin W.; Setiloane, B.P.; Journal of the American Chemical Society; vol. 104; nb. 14; (1982); p.

3917 - 3923 View in Reaxys

Br

Sn

Rx-ID: 2297170 View in Reaxys 232/513 Yield

Conditions & References With hydrogenchloride, chloroamine-T, sodium bromide in ethanol, water, Time= 0.25h, T= 0 °C Adam, Michael J.; Ruth, Thomas J.; Pate, Brian D.; Hall, Laurance D.; Journal of the Chemical Society, Chemical Communications; nb. 11; (1982); p. 625 - 626 View in Reaxys O–

O N

N

N+

Br

Cl

O

Rx-ID: 2327079 View in Reaxys 233/513 Yield 19 % Chromat.

Conditions & References With copper(II) nitrate, sodium bromide, lithium chloride, tin(ll) chloride in 1,4-dioxane, water, Time= 0.0833333h, Ambient temperature, other reagents, other time; other arenediazonium nitrates, Product distribution, Mechanism Galli, Carlo; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1982); p. 1139 - 1142 View in Reaxys

Br

Cl –

Br

Rx-ID: 3151139 View in Reaxys 234/513 Yield

Conditions & References in gas, T= 26 °C , p= 0 - 0.3Torr , Equilibrium constant French, M. A.; Ikuta, S.; Kebarle, P.; Canadian Journal of Chemistry; vol. 60; (1982); p. 1907 - 1918 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O O

Br

O

HO

Cl

O

Rx-ID: 3938116 View in Reaxys 235/513 Yield

Conditions & References

2.4 % Chro- With chloride, copper(I), bromide, copper(II) nitrate in water, acetic acid, Time= 3h, T= 100 °C , other solvent, other temperamat., 32 % ture, Product distribution Chromat., 4 % Chromat. Galli, Carlo; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1982); p. 1139 - 1142 View in Reaxys

O Br

NH

Rx-ID: 25060062 View in Reaxys 236/513 Yield

Conditions & References 7 : 3-diethylamino-6-ethyl-7-anilinofluoran STR15 Then excess bromobenzene was recovered by means of steam distillation, and the remaining solid [crude 3-methoxy-6(N-acetylanilino)ethylbenzene] was filtered off, mixed, without purifying, with 140 ml. of a 10 percent aqueous solution of caustic soda and heated in the autoclave to 200° C. for 8 hours.

After cooling, an oil layer was separated from it and purified by means of distillation under reduced pressure.

Then 14.8 g. (66.0 percent of theoretical) of 3-methoxy-6-anilinoethylbenzene was obtained as a light yellow oily substance having a boiling point of 185° to 215° C./13 mmHg, and the formula: STR16 Patent; Yamamoto Kagaku Gosei Kabushiki Kaisha; US4330473; (1982); (A) English View in Reaxys

Br

Br Sn

Br

Br

Br

Sn

Rx-ID: 26368952 View in Reaxys 237/513 Yield

Conditions & References Devaud, Marguerite; Lepousez, Patrice; Journal of Chemical Research, Synopses; (1982); p. 100 - 101 ; (from Gmelin) View in Reaxys

Sn

Br

S

S

Sn Br

Rx-ID: 26843210 View in Reaxys 238/513 Yield

Conditions & References With bromine in tetrachloromethane, to soln. of Sn compd. Br 2 added dropwise at 0 °C Wardell, James L.; Wigzell, John McM.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1982); p. 2321 - 2326 ; (from Gmelin) View in Reaxys

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Br S

S Sn Br

Sn

Rx-ID: 26949555 View in Reaxys 239/513 Yield

Conditions & References With bromine in tetrachloromethane, to soln. of Sn compd. Br2 added dropwise at 0 °C Wardell, James L.; Wigzell, John McM.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1982); p. 2321 - 2326 ; (from Gmelin) View in Reaxys

S

S

Br Sn Br

Sn

Rx-ID: 26950441 View in Reaxys 240/513 Yield

Conditions & References With bromine in tetrachloromethane, to soln. of Sn compd. Br2 added dropwise at 0 °C Wardell, James L.; Wigzell, John McM.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1982); p. 2321 - 2326 ; (from Gmelin) View in Reaxys O

O

Cl

Cl

Cl

Cl

S Br

Br

N Br

Rx-ID: 1736303 View in Reaxys 241/513 Yield

Conditions & References

19 % Chromat.

in dichloromethane, T= 400 °C , Product distribution, Mechanism Roberts, John T.; Rittberg, Barry R.; Kovacic, Peter; Journal of Organic Chemistry; vol. 46; nb. 20; (1981); p. 3988 - 3991 View in Reaxys

N Br

N

N

Rx-ID: 1975011 View in Reaxys 242/513 Yield

Conditions & References With chloro-trimethyl-silane, lithium bromide in acetonitrile, Time= 0.333333h, T= 60 °C Ku, Hao; Barrio, Jorge R.; Journal of Organic Chemistry; vol. 46; (1981); p. 5239 - 5241 View in Reaxys

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O

Br

O

Si

N O

Rx-ID: 2184157 View in Reaxys 243/513 Yield

Conditions & References With N-Bromosuccinimide in dichloromethane, Time= 13h, Ambient temperature Hosomi, Akira; Iijima, Susumu; Sakurai, Hideki; Chemistry Letters; (1981); p. 243 - 246 View in Reaxys

I+ Br–

Br

I

Rx-ID: 2429217 View in Reaxys 244/513 Yield

Conditions & References With mercury in acetonitrile, Time= 22h, T= 45 °C , other temperatures, Ea, ΔS298 K, Kinetics, Thermodynamic data Kim, T. L.; Ptitsyna, O. A.; Butin, K. P.; Reutov, O. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 30; nb. 12; (1981); p. 2244 - 2247; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1981); p. 2699 - 2703 View in Reaxys Br

Br N Br

N

N

N

Br

Rx-ID: 2557058 View in Reaxys 245/513 Yield

Conditions & References

35 %

With aluminium trichloride, T= 170 - 200 °C Robev, Stefan K.; Tetrahedron Letters; vol. 22; (1981); p. 345 - 348 View in Reaxys

Si

Si

Br

Si

Si

Br

Br

Si

Si Br

Rx-ID: 2835369 View in Reaxys 246/513 Yield 96 %

Conditions & References With bromine, Time= 2h, T= 60 °C Wiberg, Nils; Preiner, Gerhard; Schieda, Oswald; Chemische Berichte; vol. 114; nb. 6; (1981); p. 2087 - 2103 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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-1 (v1)

O

N

O

N+

Br

S (v7)

O

O

HN

Cl

HO

H 2N

Rx-ID: 3016294 View in Reaxys 247/513 Yield

Conditions & References Time= 0.5h, Ambient temperature, in the absence and presence of reductant, stimulants ( SnCl2, Fe salts, ascorbic acid) and halide ions, Product distribution Galli, Carlo; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1981); p. 1459 - 1461 View in Reaxys

Br

F–

N+

Br

N

Rx-ID: 3022427 View in Reaxys 248/513 Yield

Conditions & References Time= 6h, T= 170 °C Katritzky, Alan R.; Chermprapai, Amornsri; Bravo, Susana; Patel, Ranjan C.; Tetrahedron; vol. 37; nb. 21; (1981); p. 3603 - 3607 View in Reaxys

N+

Br

F–

Br

Rx-ID: 3023777 View in Reaxys 249/513 Yield

Conditions & References Time= 6h, T= 140 °C Katritzky, Alan R.; Chermprapai, Amornsri; Bravo, Susana; Patel, Ranjan C.; Tetrahedron; vol. 37; nb. 21; (1981); p. 3603 - 3607 View in Reaxys

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I

Br

Br

Rx-ID: 4159664 View in Reaxys 250/513 Yield 12 %

Conditions & References With bis(cyclopentadienyl)titanium dichloride, sodium tetrahydroborate, air in N,N-dimethyl-formamide, Time= 24h, T= 70 °C Meunier, Bernard; Journal of Organometallic Chemistry; vol. 204; nb. 3; (1981); p. 345 - 346 View in Reaxys

H 2N

ethane-′.′-bis-sulfonic acid chloride

Br

radioactive bromine Rx-ID: 19165129 View in Reaxys 251/513

Yield

Conditions & References Reaction Steps: 2 1: 1) conc. HCl, NaNO2, 2) K2CO3 / 1) H2O, 0 deg C, 30 min, 2) ice-water 2: 60 percent Chromat. / Me3SiCl, LiBr / acetonitrile / 0.33 h / 60 °C With hydrogenchloride, chloro-trimethyl-silane, potassium carbonate, lithium bromide, sodium nitrite in acetonitrile Ku, Hao; Barrio, Jorge R.; Journal of Organic Chemistry; vol. 46; (1981); p. 5239 - 5241 View in Reaxys

Br

NH 2

cuprocyanide

Br

potassium ferro cyanide Rx-ID: 20661858 View in Reaxys 252/513

Yield

Conditions & References Reaction Steps: 2 1: 82 percent / ethanol; benzene / 16 h / Heating 2: 67 percent / 6 h / 170 °C in ethanol, benzene Katritzky, Alan R.; Chermprapai, Amornsri; Bravo, Susana; Patel, Ranjan C.; Tetrahedron; vol. 37; nb. 21; (1981); p. 3603 - 3607 View in Reaxys Reaction Steps: 2 1: 83 percent / ethanol; benzene / 16 h / Heating 2: 50 percent / 6 h / 140 °C in ethanol, benzene Katritzky, Alan R.; Chermprapai, Amornsri; Bravo, Susana; Patel, Ranjan C.; Tetrahedron; vol. 37; nb. 21; (1981); p. 3603 - 3607 View in Reaxys

H 3Si

Br

Rx-ID: 20677476 View in Reaxys 253/513 Yield

Conditions & References Reaction Steps: 2 1: dicobalt octacarbonyl / CH2Cl2 / Ambient temperature 2: 55 percent / N-bromosuccinimide / CH2Cl2 / 13 h / Ambient temperature

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With N-Bromosuccinimide, dicobalt octacarbonyl in dichloromethane Hosomi, Akira; Iijima, Susumu; Sakurai, Hideki; Chemistry Letters; (1981); p. 243 - 246 View in Reaxys

O O

Br

Si O

Rx-ID: 20677540 View in Reaxys 254/513 Yield

Conditions & References Reaction Steps: 2 1: KOH / benzene / Heating 2: 55 percent / N-bromosuccinimide / CH2Cl2 / 13 h / Ambient temperature With potassium hydroxide, N-Bromosuccinimide in dichloromethane, benzene Hosomi, Akira; Iijima, Susumu; Sakurai, Hideki; Chemistry Letters; (1981); p. 243 - 246 View in Reaxys Reaction Steps: 3 1: LiAlH4 / diethyl ether / Heating 2: dicobalt octacarbonyl / CH2Cl2 / Ambient temperature 3: 55 percent / N-bromosuccinimide / CH2Cl2 / 13 h / Ambient temperature With N-Bromosuccinimide, lithium aluminium tetrahydride, dicobalt octacarbonyl in diethyl ether, dichloromethane Hosomi, Akira; Iijima, Susumu; Sakurai, Hideki; Chemistry Letters; (1981); p. 243 - 246 View in Reaxys Cl

Cl

Si

Br

Cl

Rx-ID: 20691662 View in Reaxys 255/513 Yield

Conditions & References Reaction Steps: 3 1: chloroplatinic acid / Heating 2: KOH / benzene / Heating 3: 55 percent / N-bromosuccinimide / CH2Cl2 / 13 h / Ambient temperature With potassium hydroxide, N-Bromosuccinimide, dihydrogen hexachloroplatinate in dichloromethane, benzene Hosomi, Akira; Iijima, Susumu; Sakurai, Hideki; Chemistry Letters; (1981); p. 243 - 246 View in Reaxys Reaction Steps: 4 1: chloroplatinic acid / Heating 2: LiAlH4 / diethyl ether / Heating 3: dicobalt octacarbonyl / CH2Cl2 / Ambient temperature 4: 55 percent / N-bromosuccinimide / CH2Cl2 / 13 h / Ambient temperature With N-Bromosuccinimide, lithium aluminium tetrahydride, dihydrogen hexachloroplatinate, dicobalt octacarbonyl in diethyl ether, dichloromethane Hosomi, Akira; Iijima, Susumu; Sakurai, Hideki; Chemistry Letters; (1981); p. 243 - 246 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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N+

N

Br

Rx-ID: 144545 View in Reaxys 256/513 Yield

Conditions & References With bromide, copper(II) nitrate, ascorbic acid in water, Time= 0.5h, Ambient temperature Galli, Carlo; Tetrahedron Letters; vol. 21; (1980); p. 4515 - 4516 View in Reaxys With bromide, copper(II) nitrate, ascorbic acid in water, Time= 0.5h, Ambient temperature, further substituted educts Galli, Carlo; Tetrahedron Letters; vol. 21; (1980); p. 4515 - 4516 View in Reaxys With copper hydride, hydrogen bromide, T= 0 °C Neogi; Mitra; Journal of the Chemical Society; (1928); p. 1332 View in Reaxys With cupro salt, potassium bromide Sandmeyer; Chemische Berichte; vol. 17; (1884); p. 2651 View in Reaxys O O O

Br

Cl

Rx-ID: 1755031 View in Reaxys 257/513 Yield

Conditions & References With triphenylmethane, T= 69.9 °C , k(Br)/k(Cl), var. temp., competition const., Kinetics, Product distribution, Thermodynamic data Giese, Bernd; Stellmach, Joachim; Chemische Berichte; vol. 113; nb. 10; (1980); p. 3294 - 3302 View in Reaxys

O F

O

S

S

S O

F

O

O

O O

F

Br–

+Mg

F

Br

F

F

F

F F

Rx-ID: 1967448 View in Reaxys 258/513 Yield

Conditions & References

7 % Chromat.

in diethyl ether, T= -78 °C Creary, Xavier; Journal of Organic Chemistry; vol. 45; nb. 13; (1980); p. 2727 - 2729 View in Reaxys Br

Br

Li

Br

Br Br

Br

Br

Rx-ID: 1983368 View in Reaxys 259/513 Yield 52 %

Conditions & References in diethyl ether, Time= 5h, bath temperature 25 deg C, Further byproducts given

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Huddle, Penelope A.; Perold, Guido W.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 2617 - 2625 View in Reaxys

-1

O

N O–

(v4)

F

Br

2 Na +

O

F B FF

N+

Br

N

N

Br

O N

O

O

N O

O–

Br

Rx-ID: 2327206 View in Reaxys 260/513 Yield

Conditions & References

60 %

in methanol, T= 0 - 35 °C Lipina, E. S.; Stepanov, N. D.; Bagal, I. L.; Bodina, R. I.; Perekalin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 2059 - 2067; Zhurnal Organicheskoi Khimii; vol. 16; nb. 11; (1980); p. 2404 - 2413 View in Reaxys

-1 F F

O

N+

Br

O

N

N

B FF

Br

+ O2– Na

–O

(v4)

N

Br

O

O

O

N

N

O Br

Rx-ID: 2327207 View in Reaxys 261/513 Yield

Conditions & References

65 %

in water, Time= 0.25h, T= 0 °C Lipina, E. S.; Stepanov, N. D.; Bagal, I. L.; Bodina, R. I.; Perekalin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 2059 - 2067; Zhurnal Organicheskoi Khimii; vol. 16; nb. 11; (1980); p. 2404 - 2413 View in Reaxys

2 Na +

-1 F F

O–

N

B FF

N

O

Br

N

O

N+

Br

Br

O

–O

(v4)

N N

O

O

O Br

Rx-ID: 2327209 View in Reaxys 262/513 Yield

Conditions & References

38 %

in methanol, T= 0 - 35 °C Lipina, E. S.; Stepanov, N. D.; Bagal, I. L.; Bodina, R. I.; Perekalin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 2059 - 2067; Zhurnal Organicheskoi Khimii; vol. 16; nb. 11; (1980); p. 2404 - 2413 View in Reaxys

-1

N O

(v4)

F

+ O2– Na

–O

F B FF

Br

N

Br Br

N+

O

O

N

N O

O N O Br

Rx-ID: 2327210 View in Reaxys 263/513 Yield 70 %

Conditions & References in water, Time= 0.25h, T= 0 °C Lipina, E. S.; Stepanov, N. D.; Bagal, I. L.; Bodina, R. I.; Perekalin, V. V.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 2059 - 2067; Zhurnal Organicheskoi Khimii; vol. 16; nb. 11; (1980); p. 2404 - 2413

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

94/149

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View in Reaxys

Br Cl

Rx-ID: 2697549 View in Reaxys 264/513 Yield

Conditions & References With aluminium trichloride, bromine, Time= 0.25h Apte, D. V.; Deodhar, K. D.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol.

19; nb. 9; (1980); p. 758 - 759 View in Reaxys O

HO

H 2N

HO

Br

Br

O

Rx-ID: 3376061 View in Reaxys 265/513 Yield

Conditions & References

41 % Chromat.

With tert-Butyl thionitrate, copper(ll) bromide in acetonitrile Oae, Shigeru; Shinhama, Koichi; Kim, Yong Hae; Bulletin of the Chemical Society of Japan; vol. 53; nb. 4; (1980); p. 1065 1069 View in Reaxys

Br

H 2N

Br

Br

Br

Br

Br

Rx-ID: 3377089 View in Reaxys 266/513 Yield

Conditions & References With tert.-butylnitrite, copper(ll) bromide in acetonitrile, Time= 0.25h, T= 65 °C , Product distribution Doyle, Michael P.; Lente, Michael A. van; Mowat, Rex; Fobare, William F.; Journal of Organic Chemistry; vol. 45; nb. 13; (1980); p. 2570 - 2575 View in Reaxys F

F F

F

F

F

F

F

Mg

Br

O O F F

F

F F

F

Br

F

F

F F F

F

F

F F

F

F

F

F

F

F

F

F

O

Br

F

F F F

F F

F O

F

F F

Br

F F

F

F F

F

O

F

O

Br F

F

F O

F

F

F

F

F F

F F

O

F F

Rx-ID: 26754360 View in Reaxys 267/513 Yield 8 %, 47.5 %, 7 %

Conditions & References in diethyl ether, -20°C, 12 d

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Gopal; Tamborski; Journal of Fluorine Chemistry; vol. 13; (1979); p. 337,339, 340, 344, 348 ; (from Gmelin) View in Reaxys 8 %, 47.5 %, 7 %

in diethyl ether, -20°C, 12 d vol. F: PerFHalOrg.SVol.1; 2.2, page 20 - 27 ; (from Gmelin) View in Reaxys

HN

Br

S O

Rx-ID: 25212299 View in Reaxys 268/513 Yield

Conditions & References

63%

27 : EXAMPLE 27 EXAMPLE 27 Example 21 was carried out with 2-bromothiophene rather than bromobenzene and N-phenyl-2-thiophenecarboxamide was formed in 63percent yield, m.p. 139°-149°.

Patent; The University of Delaware; US3988358; (1976); (A) English View in Reaxys

63%

7 : EXAMPLE 7 EXAMPLE 7 Example 1 was carried out with 2-bromothiophene rather than bromobenzene and N-phenyl-2-thiophenecarboxamide was formed in 63percent yield, m.p. 139°-140°.

Patent; University of Delaware; US4128554; (1978); (A) English View in Reaxys

Sb

Br

Br

Sb

Br

Br

Rx-ID: 26525033 View in Reaxys 269/513 Yield

Conditions & References

91.7 %

heating in N2 atm. at 220-230°C for 30 min, distn. at 10-15 Torr at 170-180°C Reinert, G. B.; Prax. Naturwiss. III; vol. 22; (1973); p. 169 - 182 ; (from Gmelin) View in Reaxys vol. Sb: Org.Comp.2; 1.2.1.1.5.2, page 24 - 25 ; (from Gmelin) View in Reaxys

Br H

HH (v3) H H H O (v3) H H Cr O H (v6) H H Br H HH HHH H Br H H O

Br

(v3)

H

H

H

H

Rx-ID: 26623638 View in Reaxys 270/513 Yield

Conditions & References in neat (no solvent), byproducts: C6H6, C6H5C6H5; heating;

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Sato, M.; Ishida, Y.; Nippon Kagaku Zasshi; vol. 91; (1970); p. 173 - 176 ; (from Gmelin) View in Reaxys in neat (no solvent), byproducts: C6H6, C6H5C6H5; heating; vol. Cr: Org.Verb.; 1.1.1.2.6, page 16 - 21 ; (from Gmelin) View in Reaxys Br

H

Br Br

HH (v3) H H H O (v3) H H Cr O H (v6) H H H H H H HH H H H O

Br

(v3)

H

H

H

H

Rx-ID: 26623618 View in Reaxys 271/513 Yield

Conditions & References With H2O in neat (no solvent) Stolze, G.; Haehle, J.; Journal of Organometallic Chemistry; vol. 5; (1966); p. 545 - 551 ; (from Gmelin) View in Reaxys With H2O in neat (no solvent) Hein, F.; Haehle, J.; Stolze, G.; Monatsberichte der Deutschen Akademie der Wissenschaften zu Berlin; vol. 5; (1963); p. 528 530 View in Reaxys vol. Cr: Org.Verb.; 1.1.1.2.6, page 16 - 21 ; (from Gmelin) View in Reaxys

N

Br

Br

N

Rx-ID: 26401595 View in Reaxys 272/513 Yield

Conditions & References With benzene, AlBr3 in benzene, Electrolysis; 30°C vol. C: MVol.D3; 6.2.5.5, page 227 - 228 View in Reaxys Wilson, L. R.; Diss. Univ. of Kansas 1963, S. 1/89; Diss. Abstr.; vol. 25; (1964); p. 1589 ; (from Gmelin) View in Reaxys

B–

Na +

Br–

N

N S+ Br

S Br

N

N B

Rx-ID: 26603910 View in Reaxys 273/513

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

97/149

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Yield

Conditions & References byproducts: diphenyl Noeth,H.; Mikulaschek,G.; Chemische Berichte; vol. 97; (1964); p. 202 - 206 ; (from Gmelin) View in Reaxys byproducts: diphenyl vol. B: B-Verb.3; 3.4, page 63 - 64 ; (from Gmelin) View in Reaxys

O

Br N

Sn

O

O

HN

Br

Sn

C 12H 10OSn

O

Sn

O

Rx-ID: 26487729 View in Reaxys 274/513 Yield

Conditions & References in tetrachloromethane, 100°C vol. Sn: Org.Verb.1; 1.1.1.16.1.4.4, page 157 - 159 View in Reaxys Kupchik, E. J.; Lanigan, T.; Journal of Organic Chemistry; vol. 27; (1962); p. 3661 - 3665 ; (from Gmelin) View in Reaxys

Br

O–

OH O

Sn

Cl OO

Br

+Sn

O

Cl OO

Rx-ID: 26700730 View in Reaxys 275/513 Yield

Conditions & References Kinetics Eaborn, C.; Waters, J. A.; Journal of the Chemical Society; (1961); p. 542 - 547 ; (from Gmelin) View in Reaxys Kinetics vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 ; (from Gmelin) View in Reaxys

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98/149

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N N

Li O

Br

N N

N

benzoic acid and 4-bromo-2-methyl-2H-pyrazole-3-carboxylic acid

Br

N O HO

Rx-ID: 5726048 View in Reaxys 276/513 Yield

Conditions & References anschl. mit CO2 bei -70grad Huettel; Schoen; Justus Liebigs Annalen der Chemie; vol. 625; (1959); p. 55,60 View in Reaxys -1

Br

Br Hg (v3)

Br

N+

N

diphenylbromonium tetrabromomercurate(II)

Br

Rx-ID: 8275300 View in Reaxys 277/513 Yield

Conditions & References Nesmejanow; Tolstaja; Doklady Akademii Nauk SSSR; vol. 128; (1959); p. 726; Doklady Chemistry; 124-129<1959>817 View in Reaxys Br O–

HO

HO

S OO

Br

O

Br

N+ N

Rx-ID: 57082 View in Reaxys 278/513 Yield

Conditions & References Product distribution DeTar; Kosuge; Journal of the American Chemical Society; vol. 80; (1958); p. 6072,6073,6075 View in Reaxys Br O–

HO

HO

S OO

oxygen

Br

O

Br

N+ N

Rx-ID: 7976908 View in Reaxys 279/513 Yield

Conditions & References Product distribution DeTar; Kosuge; Journal of the American Chemical Society; vol. 80; (1958); p. 6072,6073,6075 View in Reaxys

Br+ I–

Br

I

Rx-ID: 628781 View in Reaxys 280/513

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99/149

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Yield

Conditions & References T= 21 °C Nesmejanow et al.; Tetrahedron; vol. 1; (1957); p. 145,156 View in Reaxys Br Br

B Br

B

Br

Br

Br

Br

Rx-ID: 26368599 View in Reaxys 281/513 Yield

Conditions & References 200°C Abel, E. W.; Gerrard, W.; Lappert, M. F.; Journal of the Chemical Society; (1957); p. 5051 - 5054 View in Reaxys vol. B: B-Verb.9; 6.3.2, page 303 - 314 ; (from Gmelin) View in Reaxys

Br Na +

B–

S+

Br–

Br

S

B

Rx-ID: 26603915 View in Reaxys 282/513 Yield

Conditions & References byproducts: NaBr Boehme, H.; Boll, E.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 291; (1957); p. 160 - 163 ; (from Gmelin) View in Reaxys byproducts: NaBr vol. B: B-Verb.3; 3.3, page 54 - 63 ; (from Gmelin) View in Reaxys

Br

B

B O

Rx-ID: 31291937 View in Reaxys 283/513 Yield

Conditions & References Reaction Steps: 2 vol. B: B-Verb.9; 6.3.2, page 303 - 314 View in Reaxys Reaction Steps: 2 Abel, E. W.; Gerrard, W.; Lappert, M. F.; Journal of the Chemical Society; (1957); p. 5051 - 5054 View in Reaxys

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vol. B: B-Verb.9; 6.3.2, page 303 - 314 View in Reaxys

I+

N

Br–

O

I

Br

Rx-ID: 698724 View in Reaxys 284/513 Yield

Conditions & References T= 60 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 100 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 120 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys T= 80 °C , thermische Zersetzung, Rate constant Beringer et al.; Journal of Physical Chemistry; vol. 60; (1956); p. 141,143 View in Reaxys

Cl

O

Cl Br

Cl

Br

Br

Ag2O

Cl

Cl

Rx-ID: 5801874 View in Reaxys 285/513 Yield

Conditions & References Rice; Morganroth; Journal of Organic Chemistry; vol. 21; (1956); p. 1388 View in Reaxys

O

Li

Br

O

O Br

Rx-ID: 654227 View in Reaxys 286/513 Yield

Conditions & References Summers; Larson; Journal of the American Chemical Society; vol. 74; (1952); p. 4498 View in Reaxys

Br

Br

silver trifluoroacetate

Br

Rx-ID: 6416694 View in Reaxys 287/513 Yield

Conditions & References Haszeldine; Sharpe; Journal of the Chemical Society; (1952); p. 993,1000 View in Reaxys

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101/149

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HO Br

OH

B

Br

Br

Br

H

B HO

HO

OH

Rx-ID: 26087008 View in Reaxys 288/513 Yield

Conditions & References in acetic acid, 20percent aq. acetic acid; Kuivila; Hendrickson; Journal of the American Chemical Society; vol. 74; (1952); p. 5068 ; (from Gmelin) View in Reaxys in acetic acid vol. B: B-Verb.13; 4.7.2.3, page 196 - 203 ; (from Gmelin) View in Reaxys

O

O

H

H

Br

NaBr

O

Br

Br

Rx-ID: 6674775 View in Reaxys 289/513 Yield

Conditions & References es erfolgt elektrochemische Bromierung Bionda; Civera; Annali di Chimica (Rome, Italy); vol. 41; (1951); p. 814,817 View in Reaxys O

Br

HO

OH

B

Br

Br

Br

H

H3BO3

HO

Rx-ID: 6728571 View in Reaxys 290/513 Yield

Conditions & References T= 25 °C , Rate constant Kuivila; Easterbrook; Journal of the American Chemical Society; vol. 73; (1951); p. 4629,4630 View in Reaxys

O H

H O

Br

O

N

Br

OH

Ag+

N

O–

Br

O

O

Rx-ID: 6416674 View in Reaxys 291/513 Yield

Conditions & References Derbyshire; Waters; Journal of the Chemical Society; (1950); p. 573,576 View in Reaxys

Cl

Cl Br

Cl

Br

Br

Br

H

Cl

Rx-ID: 8213612 View in Reaxys 292/513 Yield

Conditions & References Wibaut; Haak; Recueil des Travaux Chimiques des Pays-Bas; vol. 69; (1950); p. 1387,1392 View in Reaxys

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102/149

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Cl

Br

Cl

OH

Br Br

OH

Br Br

Rx-ID: 464397 View in Reaxys 293/513 Yield

Conditions & References With aluminium trichloride, benzene Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys Cl

Cl Br

Cl

Br

Br

HO

Cl

Br

Rx-ID: 848507 View in Reaxys 294/513 Yield

Conditions & References With aluminium trichloride Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Br

Cl

Cl

Br

Br Br

OH

HO Br

Rx-ID: 848523 View in Reaxys 295/513 Yield

Conditions & References With aluminium trichloride Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Br

Cl

Br

OH

Cl Al

Br

Cl

Cl

Cl

Rx-ID: 6416665 View in Reaxys 296/513 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Br

Cl

Br

OH

Cl Al Cl

Br

Cl

Br

Rx-ID: 6416666 View in Reaxys 297/513 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

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103/149

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Cl

Br

Br

OH

Cl Al

Br

Cl

Cl

Br

Rx-ID: 6416667 View in Reaxys 298/513 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Cl

Br

Cl

Cl Al

Br

Cl

OH

Br

Cl OH

Br Br

Rx-ID: 7990333 View in Reaxys 299/513 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Br

Cl

Cl

Cl Al

Br

Cl

Br

Br

Cl OH

HO

Cl

Cl

Rx-ID: 7991981 View in Reaxys 300/513 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys

Br

Cl

Cl

Cl Al

Br

Cl

Br

Br

Cl OH

HO Br

Rx-ID: 8115860 View in Reaxys 301/513 Yield

Conditions & References Kohn; Reichmann; Journal of Organic Chemistry; vol. 12; (1947); p. 213,215 View in Reaxys O Cl

Br N

Al

Cl

Br

Cl

O

Rx-ID: 6416664 View in Reaxys 302/513 Yield

Conditions & References Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys

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104/149

2018-06-17 20:49:04

O Cl

Br N

Fe (v3)

Br

Br

Cl

Br

Cl

O

Rx-ID: 6674794 View in Reaxys 303/513 Yield

Conditions & References Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys O

Br N

Br

Br

ZnCl2

Br

O

Rx-ID: 6674804 View in Reaxys 304/513 Yield

Conditions & References Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys O

Br

Br

Br

Br

Br

OH

N HO

Br

Br

S OO

Br

O

Rx-ID: 6674805 View in Reaxys 305/513 Yield

Conditions & References Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys Br

Cl

Cl

Br

Br Br

Br

Br

Br

Br

Cl

Br

Br

Br

Rx-ID: 7449932 View in Reaxys 306/513 Yield

Conditions & References T= 30 - 35 °C Domnin; Vestnik Leningradskogo Universiteta; vol. 1; nb. 3; (1946); p. 103; ; (1948); p. 3337 View in Reaxys Domnin; Zhurnal Obshchei Khimii; vol. 16; (1946); p. 1729,1733; ; (1947); p. 5861 View in Reaxys

Cl

Cl Br–

+Mg

Br

O

O

Br

Br

Rx-ID: 61976 View in Reaxys 307/513 Yield

Conditions & References Kharasch; Sayles; Fields; Journal of the American Chemical Society; vol. 66; (1944); p. 481 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

105/149

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Cl

Cl Br

Br–

Br

+Mg

Br

O

Rx-ID: 62285 View in Reaxys 308/513 Yield

Conditions & References Kharasch; Sayles; Fields; Journal of the American Chemical Society; vol. 66; (1944); p. 481 View in Reaxys

Br

Li

Br

O

Br

Rx-ID: 653733 View in Reaxys 309/513 Yield

Conditions & References Wittig; Harborth; Chemische Berichte; vol. 77/79; (1944); p. 306,311 View in Reaxys

Br

Li

Br

Cl

O

Rx-ID: 654176 View in Reaxys 310/513 Yield

Conditions & References Wittig; Harborth; Chemische Berichte; vol. 77/79; (1944); p. 306,311 View in Reaxys

Br

Li

Br

Br

O

Rx-ID: 654177 View in Reaxys 311/513 Yield

Conditions & References Wittig; Harborth; Chemische Berichte; vol. 77; (1944); p. 320 Anm. 8 View in Reaxys

Br Br

Rx-ID: 846740 View in Reaxys 312/513 Yield

Conditions & References With iron(III) chloride Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

Br

Cl Br

Rx-ID: 846741 View in Reaxys 313/513 Yield

Conditions & References Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

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106/149

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Cl Fe (v3)

Br

Cl

Cl

Br Br

Rx-ID: 5855906 View in Reaxys 314/513 Yield

Conditions & References Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

Cl Br

Fe (v3)

Br

Cl

Cl

Rx-ID: 6416672 View in Reaxys 315/513 Yield

Conditions & References T= 100 °C Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

Cl

Br

Fe

Br

Cl

(v3)

Cl

Rx-ID: 6674183 View in Reaxys 316/513 Yield

Conditions & References Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys

Cl Fe (v3)

Br

Cl

Br

Cl

Rx-ID: 6674709 View in Reaxys 317/513 Yield

Conditions & References Nasarowa; Zukerwanik; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 236,240; ; (1945); p. 2283 View in Reaxys O–

Ag+

Br

O

Rx-ID: 536196 View in Reaxys 318/513 Yield

Conditions & References With tetrachloromethane, bromine Luettringhaus; Schade; Chemische Berichte; vol. 74; (1941); p. 1568 View in Reaxys

Br

Br

Li O

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107/149

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Br Br

Rx-ID: 654257 View in Reaxys 319/513 Yield

Conditions & References zuletzt bei Raumtemperatur Wittig; Witt; Chemische Berichte; vol. 74; (1941); p. 1474,1488 View in Reaxys

Cl

O

Cl Br

Cl

Br

Br

Cl

HO

Rx-ID: 5801873 View in Reaxys 320/513 Yield

Conditions & References beim Erwaermen von Silberbenzoat Luettringhaus; Schade; Chemische Berichte; vol. 74; (1941); p. 1567 View in Reaxys

Br

Br

Rx-ID: 846737 View in Reaxys 321/513 Yield

Conditions & References T= 500 - 650 °C Schwarz; Pflugmacher; Journal fuer Praktische Chemie (Leipzig); vol. <2> 156; (1940); p. 205,219-223 View in Reaxys

Br

C

Br

vanadium

Rx-ID: 6672368 View in Reaxys 322/513 Yield

Conditions & References Schwarz; Pflugmacher; Journal fuer Praktische Chemie (Leipzig); vol. <2> 156; (1940); p. 205,219-223 View in Reaxys Br

H O

Br

O

H O

Li

O

Rx-ID: 7059438 View in Reaxys 323/513 Yield

Conditions & References Wittig; Fuhrmann; Chemische Berichte; vol. 73; (1940); p. 1197,1217 View in Reaxys

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108/149

2018-06-17 20:49:04

Br

Br Li

O

Br

Br

O

Rx-ID: 653658 View in Reaxys 324/513 Yield

Conditions & References T= 0 °C Wittig; Pockels; Chemische Berichte; vol. 72; (1939); p. 884,886 View in Reaxys O

O

Br

S HO

Rx-ID: 783709 View in Reaxys 325/513 Yield

Conditions & References With copper(ll) bromide Varma; Parekh; Subramanium; Journal of the Indian Chemical Society; vol. 16; (1939); p. 460 View in Reaxys O

O

S

Br

copper (II)-bromide

HO

Rx-ID: 5801875 View in Reaxys 326/513 Yield

Conditions & References Varma; Parekh; Subramanium; Journal of the Indian Chemical Society; vol. 16; (1939); p. 460 View in Reaxys

Br

Br Li

nitrogen

O

Br

Br

O

Rx-ID: 5958290 View in Reaxys 327/513 Yield

Conditions & References Wittig; Pockels; Chemische Berichte; vol. 72; (1939); p. 884,886 View in Reaxys

S

sulfur

Br

Br

Br

Br

Rx-ID: 7542679 View in Reaxys 328/513 Yield

Conditions & References T= 250 - 260 °C Billman; Dougherty; Journal of the American Chemical Society; vol. 61; (1939); p. 387 View in Reaxys

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109/149

2018-06-17 20:49:04

O –O

Na +

S

Br

copper (II)-bromide

O

Rx-ID: 7976901 View in Reaxys 329/513 Yield

Conditions & References Varma; Parekh; Subramanium; Journal of the Indian Chemical Society; vol. 16; (1939); p. 460 View in Reaxys

Se

Br–

Br

Se+

Rx-ID: 589286 View in Reaxys 330/513 Yield

Conditions & References beim Erhitzen auf den Schmelzpunkt Leicester; Organic Syntheses; vol. 18; (1938); p. 28 View in Reaxys

S

S

(v2)

Hg

tetrabromoselane

Se

Br

Br

(v2)

Hg

Rx-ID: 5817824 View in Reaxys 331/513 Yield

Conditions & References Leicester; Journal of the American Chemical Society; vol. 60; (1938); p. 619 View in Reaxys

O N

N+

O

Cl –

Br

calcium carbonate

Br

Cl

Rx-ID: 8258043 View in Reaxys 332/513 Yield

Conditions & References Makin; Waters; Journal of the Chemical Society; (1938); p. 843,847 View in Reaxys O

N N

Br

Br

O

Rx-ID: 92885 View in Reaxys 333/513 Yield

Conditions & References Waters; Journal of the Chemical Society; (1937); p. 113,116 View in Reaxys

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110/149

2018-06-17 20:49:04

O

Br

N

Br N Br

O

Br

Rx-ID: 211839 View in Reaxys 334/513 Yield

Conditions & References Waters; Journal of the Chemical Society; (1937); p. 113,116 View in Reaxys

Br

Br Br

Br

Br

Rx-ID: 847492 View in Reaxys 335/513 Yield

Conditions & References langsame Neutronen.Irradiation Glueckauf; Fay; Journal of the Chemical Society; (1936); p. 392 View in Reaxys T= 150 - 180 °C Hunter; Edgar; Journal of the American Chemical Society; vol. 54; (1932); p. 2025,2026 View in Reaxys

HN

Br

4-bromo-phenylhydrazine hydrochloride

H 2N H

H N

Br

Br

NH 2

nitrogen

H

Rx-ID: 6217242 View in Reaxys 336/513 Yield

Conditions & References T= 120 °C Kenner; Knight; Chemische Berichte; vol. 69; (1936); p. 341 View in Reaxys

Br

Br

BeBr2

Br

Br

Br

Rx-ID: 6674795 View in Reaxys 337/513 Yield

Conditions & References Taboury; Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 328 View in Reaxys Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 1795; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1203 View in Reaxys

Br

Br

CdBr2

Br

Br

Br

Rx-ID: 6674796 View in Reaxys 338/513

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111/149

2018-06-17 20:49:04

Yield

Conditions & References Taboury; Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 328 View in Reaxys Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 1795; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1203 View in Reaxys

Br

Br

Br

Br

MgBr2

Br

Rx-ID: 6674799 View in Reaxys 339/513 Yield

Conditions & References Taboury; Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 328 View in Reaxys Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 1795; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1203 View in Reaxys

Br

Br

Br

Br

ZnBr2

Br

Rx-ID: 6674803 View in Reaxys 340/513 Yield

Conditions & References Taboury; Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 328 View in Reaxys Pajeau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 202; (1936); p. 1795; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 204; (1937); p. 1203 View in Reaxys

(v1)

Br

Ag

Br

Rx-ID: 26437204 View in Reaxys 341/513 Yield

Conditions & References in diethyl ether, reaction time several hours, subsequently hydrolysis; vol. Ag: MVol.B5; 1.1.3, page 8 - 12 ; (from Gmelin) View in Reaxys in diethyl ether Gilman, H.; Straley, J. M.; Rec. Trav. Chim.; vol. 55; (1936); p. 821 - 834 ; (from Gmelin) View in Reaxys

Cl

O

Cl

HO

OH

Br

Cl

Cl

Br

H 2N 2 O

O

Rx-ID: 61123 View in Reaxys 342/513 Yield

Conditions & References Bockemueller; Hoffmann; Justus Liebigs Annalen der Chemie; vol. 519; (1935); p. 165,191 View in Reaxys

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112/149

2018-06-17 20:49:04

O

O Br–

S O

+Mg

Br

O

O

Rx-ID: 102233 View in Reaxys 343/513 Yield

Conditions & References Suter; Gerhart; Journal of the American Chemical Society; vol. 57; (1935); p. 109 View in Reaxys

Cl

Br–

I

+Mg

Cl

I

Br

Cl

Rx-ID: 304631 View in Reaxys 344/513 Yield

Conditions & References Le Fevre; Markham; Journal of the Chemical Society; (1934); p. 703 View in Reaxys Melnikow; Zhurnal Obshchei Khimii; vol. 5; (1935); p. 28,29; Chem. Zentralbl.; vol. 107; nb. II; (1936); p. 2896 View in Reaxys Br

O

HO

O

OH

O Br

Br

H 2N 2 O

O

HO

HO

Rx-ID: 377456 View in Reaxys 345/513 Yield

Conditions & References T= 20 °C Bockemueller; Hoffmann; Justus Liebigs Annalen der Chemie; vol. 519; (1935); p. 165,191 View in Reaxys Br

Br Se

(v2)

Hg

Se

Br

Br

(v2)

Hg

Rx-ID: 762234 View in Reaxys 346/513 Yield

Conditions & References Leicester; Journal of the American Chemical Society; vol. 57; (1935); p. 1901 View in Reaxys

Br

Br

Br

aqueous iron salts

Rx-ID: 6416681 View in Reaxys 347/513 Yield

Conditions & References Menke; ; vol. 31; (1934); p. 344 View in Reaxys

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113/149

2018-06-17 20:49:04

Br

Br

Br

Br

selenium

Br

Rx-ID: 6674800 View in Reaxys 348/513 Yield

Conditions & References O'Kelly; Journal of the American Chemical Society; vol. 56; (1934); p. 2783 View in Reaxys

Br

Br

Br

Br

tellane

Br

Rx-ID: 6674801 View in Reaxys 349/513 Yield

Conditions & References O'Kelly; Journal of the American Chemical Society; vol. 56; (1934); p. 2783 View in Reaxys

Br

Br

tellane

Br

Br

iron

Br

Rx-ID: 6674802 View in Reaxys 350/513 Yield

Conditions & References O'Kelly; Journal of the American Chemical Society; vol. 56; (1934); p. 2783 View in Reaxys

Ag+

Br

2 (v1)

Ag

Br

Br

O–

O N O

Rx-ID: 26552671 View in Reaxys 351/513 Yield

Conditions & References With copper(II) sulfate in water, react. with CuSO4 in H2O, addn. of Br2; Challenger, E.; Richards, O. V.; Journal of the Chemical Society; (1934); p. 405 - 411 View in Reaxys vol. Ag: MVol.B5; 1.1.3, page 8 - 12 ; (from Gmelin) View in Reaxys O O

Br–

+Mg

O

O Br O

Br

O

O

Rx-ID: 171856 View in Reaxys 352/513 Yield

Conditions & References Howk; McElvain; Journal of the American Chemical Society; vol. 55; (1933); p. 3372,3377 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

114/149

2018-06-17 20:49:04

HN

Br

H 2N

Rx-ID: 724323 View in Reaxys 353/513 Yield

Conditions & References With ferric(III) bromide Seide; Scherlin; Bras; Journal fuer Praktische Chemie (Leipzig); vol. <2> 138; (1933); p. 55,65 View in Reaxys

H

H

HN

O

Br

iron (III)-bromide

H 2N

Rx-ID: 5801876 View in Reaxys 354/513 Yield

Conditions & References Seide; Scherlin; Bras; Journal fuer Praktische Chemie (Leipzig); vol. <2> 138; (1933); p. 55,65 View in Reaxys O

O

O

Br–

+Mg

Br

O

Br

O

O

O

meso-2.3-dibenzoyl-succinic acid diethyl ester

Rx-ID: 7455357 View in Reaxys 355/513 Yield

Conditions & References Howk; McElvain; Journal of the American Chemical Society; vol. 55; (1933); p. 3372,3377 View in Reaxys

–O

Br

Br

O

O

Ag+

O

Br

Rx-ID: 8259883 View in Reaxys 356/513 Yield

Conditions & References T= 20 °C Birckenbach; Goubeau; Chemische Berichte; vol. 66; (1933); p. 1285,1287 View in Reaxys

–O

Br

Br

O

Ag+

Br

Rx-ID: 6416671 View in Reaxys 357/513 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

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115/149

2018-06-17 20:49:04

O Br

Br

Ag+

O–

N

Br

O

Rx-ID: 6416673 View in Reaxys 358/513 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

-2 (v1)

O

Br

Br

O

(v1)

Br

Cu 2+

S O

O

Rx-ID: 6416675 View in Reaxys 359/513 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys -2 (v1)

O

Br

Br

Br

Hg 2+ S (v1)

O

O O

Rx-ID: 6416676 View in Reaxys 360/513 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

Br

Br

Ag2SO4

Br

Rx-ID: 6416678 View in Reaxys 361/513 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

Br

Br

AgClO4

Br

Rx-ID: 6416679 View in Reaxys 362/513 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

Br

Br

AgClO4

MgO

Br

Rx-ID: 6416691 View in Reaxys 363/513 Yield

Conditions & References Birckenbach; Goubeau; Chemische Berichte; vol. 65; (1932); p. 395,399; Chemische Berichte; vol. 66; (1933); p. 1280,1284 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

116/149

2018-06-17 20:49:04

Br

Br

Br

Rx-ID: 848945 View in Reaxys 364/513 Yield

Conditions & References With bromine, pyrographite Nikolajew; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 1035; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 1428 View in Reaxys

Br

Br

Br

Br

charcoal

Br

Rx-ID: 6674797 View in Reaxys 365/513 Yield

Conditions & References Nikolajew; Zhurnal Obshchei Khimii; vol. 1; (1931); p. 1035; Chem. Zentralbl.; vol. 104; nb. I; (1933); p. 1428 View in Reaxys

Cl

Br Br

Al

HO

Br

Cl

Cl OH

HO Br

Br

Rx-ID: 7067184 View in Reaxys 366/513 Yield

Conditions & References Kohn; Monatshefte fuer Chemie; vol. 58; (1931); p. 108,110 View in Reaxys

Br

Mg

Br

Br

Rx-ID: 7976898 View in Reaxys 367/513 Yield

Conditions & References Gilman; Brown; Journal of the American Chemical Society; vol. 52; (1930); p. 1181,1185 View in Reaxys Fleck; Justus Liebigs Annalen der Chemie; vol. 276; (1893); p. 138 View in Reaxys O O

O

Br–

S

+Mg

S

Br

O

HO

Br

Rx-ID: 171560 View in Reaxys 368/513 Yield

Conditions & References Gilman; Fothergill; Journal of the American Chemical Society; vol. 51; (1929); p. 3506 View in Reaxys O

O

Br–

S

+Mg

Br

Br

Rx-ID: 333632 View in Reaxys 369/513 Yield

Conditions & References With diethyl ether

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117/149

2018-06-17 20:49:04

Gilman; Fothergill; Journal of the American Chemical Society; vol. 51; (1929); p. 3506 View in Reaxys

Sn

Br

Rx-ID: 421690 View in Reaxys 370/513 Yield

Conditions & References With bromine Bost; Borgstrom; Journal of the American Chemical Society; vol. 51; (1929); p. 1924 View in Reaxys

Br

phenyl tin tribromoide

Rx-ID: 6416693 View in Reaxys 371/513 Yield

Conditions & References With bromine Kotscheschkow; Chemische Berichte; vol. 62; (1929); p. 997,998; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol.

61; (1929); p. 1388,1390; Chem. Zentralbl.; vol. 101; nb. II; (1930); p. 548 View in Reaxys

Br S

S

Al

Br

diselenium dibromide

Br

Se

Se Br

Se

Rx-ID: 6676513 View in Reaxys 372/513 Yield

Conditions & References Loevenich; Sipmann; Journal fuer Praktische Chemie (Leipzig); vol. <2> 124; (1929); p. 132 View in Reaxys

Br

diphenylmono and -diselenide

Rx-ID: 6728058 View in Reaxys 373/513 Yield

Conditions & References With carbon disulfide, aluminum tri-bromide, selenium dibromide Loevenich; Sipmann; Journal fuer Praktische Chemie (Leipzig); vol. <2> 124; (1929); p. 132 View in Reaxys

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118/149

2018-06-17 20:49:04

Cl

Cl Si

Br

N H

Cl

Br

Si

Si

Br

O

Si

Si

Br

Rx-ID: 7879231 View in Reaxys 374/513 Yield

Conditions & References Reynolds; Bigelow; Kraus; Journal of the American Chemical Society; vol. 51; (1929); p. 3068 Anm:6 View in Reaxys

Sn

Br

Br

Br

Rx-ID: 7976897 View in Reaxys 375/513 Yield

Conditions & References Bost; Borgstrom; Journal of the American Chemical Society; vol. 51; (1929); p. 1924 View in Reaxys

Br–

+Mg

hydroxylamine

O

Br

phenol and aniline

Rx-ID: 8427647 View in Reaxys 376/513 Yield

Conditions & References Product distribution Weissberger; Fasold; Bach; Journal fuer Praktische Chemie (Leipzig); vol. <2> 124; (1929); p. 29 View in Reaxys

3

Br– 3+Sn

bromine

Br

Rx-ID: 8469585 View in Reaxys 377/513

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119/149

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Yield

Conditions & References Kotscheschkow; Chemische Berichte; vol. 62; (1929); p. 997,998; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol.

61; (1929); p. 1388,1390; Chem. Zentralbl.; vol. 101; nb. II; (1930); p. 548 View in Reaxys

Br

aqueous solution of benzenediazonium bromide

Rx-ID: 6416682 View in Reaxys 378/513 Yield

Conditions & References With zinc dibromide Patent; Kuhn; Eichenberger; DE541255; (1928); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 434,436 View in Reaxys

N

N+

Cl –

copper hydrogen

hydrogen bromide

Br

Rx-ID: 8265030 View in Reaxys 379/513 Yield

Conditions & References T= 0 °C , reagieren die Benzoldiazoniumsalze Neogi; Mitra; Journal of the Chemical Society; (1928); p. 1332 View in Reaxys

Br Br

Br

Br

Br

Rx-ID: 278688 View in Reaxys 380/513 Yield

Conditions & References With ethanol, iodine, magnesium, Zersetzen des Reaktionsprodukts mit Wasser Salkind; Rogowina; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 1015; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 2939 View in Reaxys

O O

O O

Br

HO

O

Rx-ID: 857576 View in Reaxys 381/513 Yield

Conditions & References With phosphorus(V) oxybromide, T= 192 °C Reynhart; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 67 View in Reaxys

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120/149

2018-06-17 20:49:04

O O

phosphorus oxybromide

O O

HO

O

OH

Br

H 2N 2 O

HO

Rx-ID: 6683412 View in Reaxys 382/513 Yield

Conditions & References T= 192 °C Reijnhart; Recueil des Travaux Chimiques des Pays-Bas; vol. 46; (1927); p. 65 View in Reaxys

Br

Br

magnesium

O

Br

4.4'-dibromo-diphenyl Rx-ID: 7443239 View in Reaxys 383/513

Yield

Conditions & References nachfolgend Zersetzung des Reaktionsprodukts mit Wasser Salkind; Rogowina; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 1015; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 2939 View in Reaxys Pink; Journal of the Chemical Society; vol. 123; (1923); p. 3418 View in Reaxys Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 136; (1903); p. 1138; Bulletin de la Societe Chimique de France; vol. <3>31; (1904); p. 25 View in Reaxys Quelet; Bulletin de la Societe Chimique de France; vol. <4>41; (1927); p. 934,936 View in Reaxys

I

I

O Br

magnesium

Br

Br

Rx-ID: 7449724 View in Reaxys 384/513 Yield

Conditions & References Zersetzen des Reaktionsprodukts mit Wasser Salkind; Rogowina; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 59; (1927); p. 1015; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 2939 View in Reaxys

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121/149

2018-06-17 20:49:04

Cl

Cl Br

Sn

Cl

Br

Br

Sn Br

Cl

Rx-ID: 8251548 View in Reaxys 385/513 Yield

Conditions & References T= 0 °C Bullard; Robinson; Journal of the American Chemical Society; vol. 49; (1927); p. 1371 View in Reaxys

O

Br–

+Mg

O

O

O

Br

Rx-ID: 171181 View in Reaxys 386/513 Yield

Conditions & References Kohler, Butler; Journal of the American Chemical Society; vol. 48; (1926); p. 1045 View in Reaxys

Br

O–

Br

Br

Na +

Br

Br

Rx-ID: 357279 View in Reaxys 387/513 Yield

Conditions & References low-melting 1.2.3.4-tetrabromo-cyclohexane Harries; Chemische Berichte; vol. 45; (1912); p. 811 View in Reaxys Hofmann; Damm; ; vol. 2; p. 120; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 2343 View in Reaxys Cl Cl

Br

Br

Br

OH

Br

Br

OH

Br

Rx-ID: 418538 View in Reaxys 388/513 Yield

Conditions & References With aluminium trichloride, benzene Kohn; Zandmann; Monatshefte fuer Chemie; vol. 47; (1926); p. 376 View in Reaxys

low-melting 1.2.3.4-tetrabromo-cyclohexane

Br

Rx-ID: 6416689 View in Reaxys 389/513

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Yield

Conditions & References With sodium ethanolate Hofmann,F.; Damm; ; vol. 2; p. 121; Chem. Zentralbl.; vol. 97; nb. I; (1926); p. 2343 View in Reaxys Cl Cl Br

Cl Al

Br

Br

Cl

Cl

Br

OH Br

OH

Br

Rx-ID: 8115290 View in Reaxys 390/513 Yield

Conditions & References Kohn; Zandmann; Monatshefte fuer Chemie; vol. 47; (1926); p. 376 View in Reaxys

Br Cl

OH

Rx-ID: 22117629 View in Reaxys 391/513 Yield

Conditions & References Reaction Steps: 2 1: iron powder; bromine 2: aluminium chloride; benzene With aluminium trichloride, bromine, iron, benzene Kohn; Zandmann; Monatshefte fuer Chemie; vol. 47; (1926); p. 376 View in Reaxys

O N

Br

Br

O

Rx-ID: 847611 View in Reaxys 392/513 Yield

Conditions & References With aluminium trichloride Sherrill; Journal of the American Chemical Society; vol. 46; (1924); p. 2756 View in Reaxys

O

Cl

O

Al

Cl

O

N N

Br

Br

O N

O

Cl

O

Rx-ID: 6672125 View in Reaxys 393/513 Yield

Conditions & References Sherrill; Journal of the American Chemical Society; vol. 46; (1924); p. 2756 View in Reaxys

Cl

O

Al Cl

Cl

N

Br

O

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123/149

2018-06-17 20:49:04

O

H

O

O

HO

N Br

O

Rx-ID: 7063351 View in Reaxys 394/513 Yield

Conditions & References Produkt: Nitromethan, analog verlaufen die Reaktionen mit Brombenzol, Chlorbenzol und Anisol in Schwefelkohlenstoff Sherrill; Journal of the American Chemical Society; vol. 46; (1924); p. 2756 View in Reaxys

O (v1)

–Br

(v2)

Mg+

Br

O

Br

S O

Br

O

Rx-ID: 756883 View in Reaxys 395/513 Yield

Conditions & References With diethyl ether Bert; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 176; (1923); p. 840; Bulletin de la Societe Chimique de France; vol. <4> 37; (1925); p. 1259 View in Reaxys Br Br Br

Cl Al

OH

Br

Cl

Cl

Br

Br Br

OH

Br

Rx-ID: 7048468 View in Reaxys 396/513 Yield

Conditions & References Kohn; Fink; Monatshefte fuer Chemie; vol. 44; (1923); p. 187 View in Reaxys O Br

Cl Al

Br

HO

Br

Cl

Cl Br

Br

Rx-ID: 7449806 View in Reaxys 397/513 Yield

Conditions & References Kohn; Fink; Monatshefte fuer Chemie; vol. 44; (1923); p. 185,190 View in Reaxys Br

Cl

H

Br

Bi

Br

Br

Rx-ID: 7976899 View in Reaxys 398/513 Yield

Conditions & References Challenger; Ridgway; Journal of the Chemical Society; vol. 121; (1922); p. 112 View in Reaxys

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124/149

2018-06-17 20:49:04

O O

O

S

Br–

S O

O

+Mg

Br

Cl

Rx-ID: 170885 View in Reaxys 399/513 Yield

Conditions & References Hepworth; Clapham; Journal of the Chemical Society; vol. 119; (1921); p. 1195 View in Reaxys

Br

Br–

Br Bi

+Mg

Bi

Br

Bi

Rx-ID: 624351 View in Reaxys 400/513 Yield

Conditions & References Challenger; Allpress; Journal of the Chemical Society; vol. 119; (1921); p. 916 View in Reaxys

Br

Br (v2)

Bi

Br

Hg

Bi

Br

(v2)

Hg

Hg

(v2)

Rx-ID: 762270 View in Reaxys 401/513

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

125/149

2018-06-17 20:49:04

Yield

Conditions & References weitere Produkten: Triphenylwismut, Diphenyl-′-naphthyl-wismut, 1-Brom-naphthalin Challenger; Allpress; Journal of the Chemical Society; vol. 119; (1921); p. 916 View in Reaxys

(v2)

Hg

tri-′-naphthyl bismuth dibromide

Bi

Br

Br

(v2)

Hg

Hg

(v2)

Rx-ID: 5818292 View in Reaxys 402/513 Yield

Conditions & References weitere Produkte:Triphenylwismut,Diphenyl-′-naphthyl-wismut, ′-Brom-naphthalin Challenger; Allpress; Journal of the Chemical Society; vol. 119; (1921); p. 916 View in Reaxys

Br

Cl Al

Br

Cl

Br

Br

Cl

Br

Br

Br

Rx-ID: 7449933 View in Reaxys 403/513 Yield

Conditions & References Copisarow; Journal of the Chemical Society; vol. 119; (1921); p. 447 View in Reaxys

Si Br

bromine water

Si

Rx-ID: 7976900 View in Reaxys 404/513 Yield

Conditions & References Kipping; Journal of the Chemical Society; vol. 119; (1921); p. 648 View in Reaxys

Br

H As O

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126/149

2018-06-17 20:49:04

Br As Br

hydrogen bromide

As

Rx-ID: 8426932 View in Reaxys 405/513 Yield

Conditions & References T= 250 °C , p= 17Torr Steinkopf; Schwen; Chemische Berichte; vol. 54; (1921); p. 2794,2796 View in Reaxys

I

I

Br–

+Mg

I

I

Br

triphenylmethane and 1,1,2,2-tetraphenyl-ethane Rx-ID: 8428198 View in Reaxys 406/513

Yield

Conditions & References Oddo; Binaghi; Gazzetta Chimica Italiana; vol. 51 II; (1921); p. 334 View in Reaxys

Si Br

Si

Rx-ID: 26731111 View in Reaxys 407/513 Yield

Conditions & References With bromine Kipping, F. S.; Journal of the Chemical Society; vol. 119; (1921); p. 647 - 653 ; (from Gmelin) View in Reaxys With Br2 vol. Si: MVol.C; 113, page 316 - 320 ; (from Gmelin) View in Reaxys O

Br–

+Mg

O

Cl

O Br

HO

Rx-ID: 609731 View in Reaxys 408/513

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127/149

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Yield

Conditions & References unter Eiskuehlung (Verb. 1 = 0.5 Mol in wenig Aether) Adams; Bramlet; Tendick; Journal of the American Chemical Society; vol. 42; (1920); p. 2374; Journal of the American Chemical Society; vol. 44; (1922); p. 873 View in Reaxys de Coster; ; vol. <5> 11; p. 661; Chem. Zentralbl.; 1926 3146 View in Reaxys O

phenyl magnesium bromide (2 mol)

N

little diethyl ether

O Br

HO

Rx-ID: 6683362 View in Reaxys 409/513 Yield

Conditions & References Adams; Bramlet; Tendick; Journal of the American Chemical Society; vol. 42; (1920); p. 2374; Journal of the American Chemical Society; vol. 44; (1922); p. 873 View in Reaxys

Br–

+Mg

oxygen

O

O HO

Br

p-quinone and 4,4'-dioxy-diphenyl

Rx-ID: 8427772 View in Reaxys 410/513 Yield

Conditions & References Porter; Steel; Journal of the American Chemical Society; vol. 42; (1920); p. 2652 View in Reaxys

Br

Br Br

Br

Br

Br

Br

Rx-ID: 61699 View in Reaxys 411/513 Yield

Conditions & References With diethyl ether, phenylmagnesium bromide, cis-/trans-mixture Swarts; Bulletin de la Societe Chimique de France; vol. <4>25; (1919); p. 168 View in Reaxys

Br Br

Br–

+Mg

O F

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128/149

2018-06-17 20:49:04

F Br

Rx-ID: 171015 View in Reaxys 412/513 Yield

Conditions & References Zersetzen des Reaktionsproduktes mit Wasser Swarts; Bulletin de la Societe Chimique de France; vol. <4>25; (1919); p. 168 View in Reaxys

Br Br

Br–

+Mg

O Br

Br Br

Rx-ID: 171016 View in Reaxys 413/513 Yield

Conditions & References Zersetzen des Reaktionsproduktes mit Wasser Swarts; Bulletin de la Societe Chimique de France; vol. <4>25; (1919); p. 168 View in Reaxys

Br–

+Mg

Br

Rx-ID: 624352 View in Reaxys 414/513 Yield

Conditions & References With diethyl ether, sulfur dichloride Ferrario; Bulletin de la Societe Chimique de France; vol. <4>7; (1910); p. 524 View in Reaxys With bromine Datta; Mitter; Journal of the American Chemical Society; vol. 41; (1919); p. 291 View in Reaxys

+Mg

I–

Br

Rx-ID: 737737 View in Reaxys 415/513 Yield

Conditions & References With bromine Datta; Mitter; Journal of the American Chemical Society; vol. 41; (1919); p. 291 View in Reaxys

Br

Br Br–

+Mg

O

Br

Br

Br

′.′-dibromo-ethylene Rx-ID: 6671900 View in Reaxys 416/513

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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2018-06-17 20:49:04

Yield

Conditions & References Zersetzen des Reaktionsproduktes mit Wasser Swarts; Bulletin de la Societe Chimique de France; vol. <4>25; (1919); p. 168 View in Reaxys F

F

Br–

Br

O

+Mg

Br

Br

asymm.-difluoroethylene Rx-ID: 7069299 View in Reaxys 417/513

Yield

Conditions & References Zersetzen des Reaktionsproduktes mit Wasser Swarts; Bulletin de la Societe Chimique de France; vol. <4>25; (1919); p. 168 View in Reaxys

Br–

+Mg

Br

bromine

Rx-ID: 8316867 View in Reaxys 418/513 Yield

Conditions & References Datta; Mitter; Journal of the American Chemical Society; vol. 41; (1919); p. 291 View in Reaxys

Br

Br Br–

Br

+Mg

Br

Br

′.′-dibromo-ethylene Rx-ID: 8316868 View in Reaxys 419/513

Yield

Conditions & References reagiert analog mit anderen Polyhalogenderivaten des Aethans Swarts; Bulletin de la Societe Chimique de France; vol. <4>25; (1919); p. 168 View in Reaxys

+Mg

I–

Br

bromine

Rx-ID: 8469620 View in Reaxys 420/513 Yield

Conditions & References Datta; Mitter; Journal of the American Chemical Society; vol. 41; (1919); p. 291 View in Reaxys

Br

Br

Pb

O

Br

trimethyl lead bromide

dimethyl lead dibromide Rx-ID: 8289839 View in Reaxys 421/513

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130/149

2018-06-17 20:49:04

Yield

Conditions & References T= -75 °C Gruettner; Gruettner; Chemische Berichte; vol. 51; (1918); p. 1294 View in Reaxys

Br

Br

Br

4.4'-dibromo-diphenyl

x.x-dibromo-diphenyl(?)

Rx-ID: 7458965 View in Reaxys 422/513

Yield

Conditions & References beim Leiten ueber eine rotgluehende Platinspirale Meyer,H.; Hofmann; Monatshefte fuer Chemie; vol. 38; (1917); p. 146 View in Reaxys

O Br

N

Br

Br

Br

OH

Br

O

Rx-ID: 6674793 View in Reaxys 423/513 Yield

Conditions & References Datta; Chatterjee; Journal of the American Chemical Society; vol. 38; (1916); p. 2548 View in Reaxys

N

Br–

Br

+Mg

O

O

Br

N

Rx-ID: 170814 View in Reaxys 424/513 Yield

Conditions & References nach der Zersetzung des Reaktionsprodukts mit Eis Grignard; Bellet; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p. 458 View in Reaxys Grignard; Bellet; Courtot; Annales de Chimie (Cachan, France); vol. <9> 4; (1915); p. 47 View in Reaxys Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 152; (1911); p. 389 View in Reaxys OH N

OH HO

S OO

N N

Br

Br

N

NH 2

nitrogen

N

Rx-ID: 8282616 View in Reaxys 425/513 Yield

Conditions & References Fischer,O.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 92; (1915); p. 51 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

131/149

2018-06-17 20:49:04

Br

Br

Br

Br

manganese

Br

Rx-ID: 6674798 View in Reaxys 426/513 Yield

Conditions & References Gay; Ducelliez; Raynaud; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 158; (1914); p.

1804; Bulletin de la Societe Chimique de France; vol. <4> 15; (1914); p. 737 View in Reaxys

O

Br Br

Rx-ID: 267288 View in Reaxys 427/513 Yield

Conditions & References T= 700 °C , p= 15 - 25Torr Staudinger; Anthes; Chemische Berichte; vol. 46; (1913); p. 1435 View in Reaxys

H

HN

Br

H N

Br

Br

NH 2

nitrogen

H

H 2N

Rx-ID: 6217241 View in Reaxys 428/513 Yield

Conditions & References ueber den Schmelzpunkt erhitzen Chattaway; Aldridge; Journal of the Chemical Society; vol. 99; (1911); p. 406 View in Reaxys O O S Br

sulfur

Br

Rx-ID: 7154746 View in Reaxys 429/513 Yield

Conditions & References T= 250 °C Boeeseken; Recueil des Travaux Chimiques des Pays-Bas; vol. 30; (1911); p. 142 View in Reaxys

Br

O Br

S

Br

Br

Br

O

Br

Rx-ID: 7449930 View in Reaxys 430/513 Yield

Conditions & References T= 250 °C Bourgeois; Abraham; Recueil des Travaux Chimiques des Pays-Bas; vol. 30; (1911); p. 417 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

132/149

2018-06-17 20:49:04

H

H

Br

hypobromous acid

O

Rx-ID: 6416687 View in Reaxys 431/513 Yield

Conditions & References Stark; Chemische Berichte; vol. 43; (1910); p. 672 View in Reaxys O

O S

Br

Br

Br

Br

Br

SO2Br2

Rx-ID: 7457851 View in Reaxys 432/513 Yield

Conditions & References T= 200 - 280 °C , im Einschlussrohr Boeeseken; Waterman; Recueil des Travaux Chimiques des Pays-Bas; vol. 29; (1910); p. 324 View in Reaxys -1

Br

(v2)

Br

Br

N

N+

Br

O

Br

Rx-ID: 542118 View in Reaxys 433/513 Yield

Conditions & References With ethanol Saunders; American Chemical Journal; vol. 13; (1891); p. 489 View in Reaxys Chattaway; Journal of the Chemical Society; vol. 95; (1909); p. 868 View in Reaxys Br O

N

OH

N+

HO

Br

Br

Br

Rx-ID: 639011 View in Reaxys 434/513 Yield

Conditions & References T= 80 - 100 °C , beim Behandeln von Benzoldiazoniumperbromid Chattaway; Journal of the Chemical Society; vol. 95; (1909); p. 868 View in Reaxys

HO

Br HO

Br

Br

Br

Rx-ID: 848505 View in Reaxys 435/513 Yield

Conditions & References With aluminium trichloride Kohn; Mueller; Monatshefte fuer Chemie; vol. 30; (1909); p. 407 View in Reaxys

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133/149

2018-06-17 20:49:04

Br Cl Al

HO

Cl

Br

HO

Br

Cl

Br

Rx-ID: 6208351 View in Reaxys 436/513 Yield

Conditions & References Kohn; Mueller; Monatshefte fuer Chemie; vol. 30; (1909); p. 407 View in Reaxys Br O

OH

N+

N

Br–

Br

HCl

N

N+

HO

Br

Br

Rx-ID: 6684357 View in Reaxys 437/513 Yield

Conditions & References beim Behandeln von Benzoldiazoniumperbromid Chattaway; Journal of the Chemical Society; vol. 95; (1909); p. 868 View in Reaxys

Cl

HO Al

Br HO

Br

Cl

Cl

Br

Br

Rx-ID: 6712568 View in Reaxys 438/513 Yield

Conditions & References Kohn; Mueller; Monatshefte fuer Chemie; vol. 30; (1909); p. 407 View in Reaxys

N

OH

N+

Br

HBr and ethyl bromide

bromine acetaldehyde and phenol and bromo derivatives of phenetole Rx-ID: 6728585 View in Reaxys 439/513

Yield

Conditions & References beim Kochen von Benzoldiazoniumchlorid Saunders; American Chemical Journal; vol. 13; (1891); p. 489 View in Reaxys Chattaway; Journal of the Chemical Society; vol. 95; (1909); p. 868 View in Reaxys

Si

Br

Si Br

Rx-ID: 274919 View in Reaxys 440/513 Yield

Conditions & References With bromine, T= 100 °C , dann auf 150grad

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134/149

2018-06-17 20:49:04

Ladenburg; Chemische Berichte; vol. 40; (1907); p. 2278 View in Reaxys

Br

O

aqueous KOH-solution N

NH

O

O O H

OH Br

H N

HO

O

HO

H

OH

Rx-ID: 5720211 View in Reaxys 441/513 Yield

Conditions & References Wootton; Journal of the Chemical Society; vol. 91; (1907); p. 1892 View in Reaxys

OH

HN

Br

oxygen

Br

alkali

nitrogen

H 2N

Rx-ID: 6217150 View in Reaxys 442/513 Yield

Conditions & References Chattaway; Journal of the Chemical Society; vol. 91; (1907); p. 1330; Journal of the Chemical Society; vol. 93; (1908); p. 270 View in Reaxys

Br

OH

Cl

N

Cl

HN

O

Cl

Br

H 2N

N Br

Rx-ID: 298415 View in Reaxys 443/513 Yield

Conditions & References Forster; Grossmann; Journal of the Chemical Society; vol. 89; (1906); p. 406 View in Reaxys

N

N+

copper bromide

KBr

Br

acid

Rx-ID: 6416688 View in Reaxys 444/513 Yield

Conditions & References beim Behandeln von Benzoldiazoniumsulfat Sandmeyer; Chemische Berichte; vol. 17; (1884); p. 2651 View in Reaxys Acree; Chemische Berichte; vol. 37; (1904); p. 993; American Chemical Journal; vol. 33; (1905); p. 194 View in Reaxys

HO

N

N+

Br

Cl –

Br

O

Br

Rx-ID: 56882 View in Reaxys 445/513

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References Hantzsch; Jochem; Chemische Berichte; vol. 34; (1901); p. 3340 View in Reaxys

OH

N

N+

Br

Cl –

Br

Rx-ID: 193422 View in Reaxys 446/513 Yield

Conditions & References Hantzsch; Jochem; Chemische Berichte; vol. 34; (1901); p. 3340 View in Reaxys

Br–

N

N+

HO

Br

Rx-ID: 593401 View in Reaxys 447/513 Yield

Conditions & References With water Hantzsch; Chemische Berichte; vol. 33; (1900); p. 2527,2535, 2536 View in Reaxys With hydrogen bromide Gasiorowski; Wayss; Chemische Berichte; vol. 18; (1885); p. 1939 View in Reaxys

Br

Br

Br

Rx-ID: 6416668 View in Reaxys 448/513 Yield

Conditions & References Schramm; Chemische Berichte; vol. 18; (1885); p. 607 View in Reaxys Bruner; Chem. Zentralbl.; vol. 71; nb. II; (1900); p. 257 View in Reaxys

O N

OH

bromosulfur

Br

O

Rx-ID: 6416686 View in Reaxys 449/513 Yield

Conditions & References Edinger; Goldberg; Chemische Berichte; vol. 33; (1900); p. 2884 View in Reaxys

N

N+

water

Br

Rx-ID: 6416697 View in Reaxys 450/513 Yield

Conditions & References beim Behandeln des Doppelsalzes von Benzoldiazoniumbromid mit Kupferbromuer Hantzsch; Chemische Berichte; vol. 28; (1895); p. 1752 View in Reaxys Hantzsch; Blagden; Chemische Berichte; vol. 33; (1900); p. 2550

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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View in Reaxys

Cl Al

Cl

N

Br

Cl

N

N

Br

N

N

Rx-ID: 6681861 View in Reaxys 451/513 Yield

Conditions & References Scholl; Noerr; Chemische Berichte; vol. 33; (1900); p. 1056 View in Reaxys

N

N+

water

HO

Br

nitrogen Rx-ID: 6730000 View in Reaxys 452/513

Yield

Conditions & References beim Behandeln von Benzoldiazoniumbromid (Verb. 1: 1 Mol), Product distribution Griess; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 89; Journal of the Chemical Society; vol. 20; (1867); p. 64 View in Reaxys Griess; Journal of the Chemical Society; vol. 20; (1867); p. 94; Journal fuer Praktische Chemie (Leipzig); vol. <1> 101; (1867); p. 91 View in Reaxys Hantzsch; Chemische Berichte; vol. 33; (1900); p. 2527,2535, 2536 View in Reaxys

N

N+

water

Br

copper bromide

nitrogen Rx-ID: 6730009 View in Reaxys 453/513

Yield

Conditions & References beim Behandeln des Doppelsalzes des Bromids mit Kupferbromuer Hantzsch; Chemische Berichte; vol. 28; (1895); p. 1752 View in Reaxys Hantzsch; Blagden; Chemische Berichte; vol. 33; (1900); p. 2550 View in Reaxys

I

I

H

Br

red phosphorus

Br

Rx-ID: 6801016 View in Reaxys 454/513 Yield

Conditions & References T= 250 °C

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Klages; Liecke; Journal fuer Praktische Chemie (Leipzig); vol. <2> 61; (1900); p. 322 View in Reaxys Br Br

Br

Br

Br

I

H

Br

phosphorus

Br

Rx-ID: 7449716 View in Reaxys 455/513 Yield

Conditions & References T= 302 °C Klages; Liecke; Journal fuer Praktische Chemie (Leipzig); vol. <2> 61; (1900); p. 322 View in Reaxys Br

Br

Br

I

H

Br

phosphorus

Br

Rx-ID: 7449717 View in Reaxys 456/513 Yield

Conditions & References T= 302 °C Klages; Liecke; Journal fuer Praktische Chemie (Leipzig); vol. <2> 61; (1900); p. 322 View in Reaxys

Br

Br

Br

amalgamated aluminium

Rx-ID: 6416680 View in Reaxys 457/513 Yield

Conditions & References Cohen; Dakin; Journal of the Chemical Society; vol. 75; (1899); p. 894 View in Reaxys Br N

HO

N

O

O–

O

Br

Br

N+ O

Rx-ID: 57005 View in Reaxys 458/513 Yield

Conditions & References Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys Br O–

O N

HO

N

Br

N+ O

Rx-ID: 57011 View in Reaxys 459/513 Yield

Conditions & References Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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2018-06-17 20:49:04

O N+

2

HO

Br

O–

N –

O

Br

S OO

Br

Rx-ID: 57115 View in Reaxys 460/513 Yield

Conditions & References Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys

N+

2

HO

O–

N –O

Br

S OO

Br

Rx-ID: 57118 View in Reaxys 461/513 Yield

Conditions & References Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys Br O–

O OH

N N

Br

N+ O

Rx-ID: 193644 View in Reaxys 462/513 Yield

Conditions & References Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys O–

O OH

N

N+

N

Br

Br

O

Rx-ID: 193647 View in Reaxys 463/513 Yield

Conditions & References Griess; Journal of the Chemical Society; vol. 20; (1867); p. 94; Journal fuer Praktische Chemie (Leipzig); vol. <1> 101; (1867); p. 91 View in Reaxys Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys Br O–

O OH

N N

Br

N+ O

Rx-ID: 193650 View in Reaxys 464/513 Yield

Conditions & References Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys Br O–

OH

HO

S OO

Br

N+ N

Rx-ID: 193776 View in Reaxys 465/513

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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2018-06-17 20:49:04

Yield

Conditions & References Griess; Journal of the Chemical Society; vol. 20; (1867); p. 94; Journal fuer Praktische Chemie (Leipzig); vol. <1> 101; (1867); p. 91 View in Reaxys Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys

OH

N+

2

O–

N

Br

S OO

–O

Br

Rx-ID: 193830 View in Reaxys 466/513 Yield

Conditions & References Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys

OH

N+

2

O–

N –O

Br

S OO

Br

Rx-ID: 193834 View in Reaxys 467/513 Yield

Conditions & References Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys

m-bromo-benzenediazonium-sulfate

Br

Rx-ID: 6416690 View in Reaxys 468/513 Yield

Conditions & References With ethanol Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys

p-bromo-benzenediazonium-sulfate

Br

Rx-ID: 6416692 View in Reaxys 469/513 Yield

Conditions & References With ethanol Cameron; American Chemical Journal; vol. 20; (1898); p. 236,238 View in Reaxys

N N

N+

KBr

Br

copper sulfate

N

Rx-ID: 6684016 View in Reaxys 470/513 Yield

Conditions & References beim Behandeln von Benzoldiazoniumsulfat an Kupfer-Elektroden.Electrolysis Votocek; Zenisek; Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie; vol. 5; (1898); p. 486; Chem. Zentralbl.; vol. 70; nb. I; (1899); p. 1145 View in Reaxys

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OH O

P

Br

Br

metaphosphoric acid

HO

Rx-ID: 7923792 View in Reaxys 471/513 Yield

Conditions & References Michaelis; Justus Liebigs Annalen der Chemie; vol. 293; (1896); p. 265 View in Reaxys

syn-benzenediazo bromide-cupro bromide

Br

Rx-ID: 6416696 View in Reaxys 472/513 Yield

Conditions & References With water Hantzsch; Chemische Berichte; vol. 28; (1895); p. 1752 View in Reaxys

N Br

N Br

Br2Cu 2

Rx-ID: 26649674 View in Reaxys 473/513 Yield

Conditions & References With water in water, byproducts: N2; decompn.; Hanitzsch, A.; Ber.; vol. 28; (1895); p. 1734 - 1753 View in Reaxys vol. Cu: MVol.B1; 164, page 362 - 364 ; (from Gmelin) View in Reaxys

Br

Cl Al

Cl

Cl

Br

Br

Rx-ID: 5856162 View in Reaxys 474/513 Yield

Conditions & References Schramm; Chemische Berichte; vol. 26; (1893); p. 1706 View in Reaxys

Cl Al

Cl

′.′-dibromo-′-phenyl-ethane

Cl

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Br

Rx-ID: 6681979 View in Reaxys 475/513 Yield

Conditions & References Schramm; Chemische Berichte; vol. 26; (1893); p. 1706 View in Reaxys

Br

11.12-dibromo-ethylbenzene

Rx-ID: 7158182 View in Reaxys 476/513 Yield

Conditions & References With aluminium trichloride, benzene Schramm; Chemische Berichte; vol. 26; (1893); p. 1706 View in Reaxys

N+

N

copper sulfate

sodium hypophosphite

KBr

Br

acid

Rx-ID: 6416695 View in Reaxys 477/513 Yield

Conditions & References beim Behandeln von Benzoldiazoniumsulfat Angeli; Gazzetta Chimica Italiana; vol. 21 II; (1891); p. 260 View in Reaxys

Br

benzenediazonium-perbromide

O

Br

Rx-ID: 6676367 View in Reaxys 478/513 Yield

Conditions & References With ethanol Saunders; American Chemical Journal; vol. 13; (1891); p. 489 View in Reaxys

Br–

N

N+

Br

Rx-ID: 593399 View in Reaxys 479/513 Yield

Conditions & References With copper Gattermann; Chemische Berichte; vol. 23; (1890); p. 1220 View in Reaxys

N

N+

acid

copper-powder

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water

copper bromide

2018-06-17 20:49:04

Br

Rx-ID: 6416698 View in Reaxys 480/513 Yield

Conditions & References beim Behandeln von Benzoldiazoniumsulfat Gattermann; Chemische Berichte; vol. 23; (1890); p. 1220 View in Reaxys

Br N

Br

N+

Br

zinc copper Br

Rx-ID: 6671899 View in Reaxys 481/513 Yield

Conditions & References beim Behandeln von Benzoldiazoniumchlorid Oddo; Gazzetta Chimica Italiana; vol. 20; (1890); p. 639 View in Reaxys

N

N+

HO

Br

HBr

Rx-ID: 6712569 View in Reaxys 482/513 Yield

Conditions & References beim Behandeln von Benzoldiazoniumbromid Oddo; Gazzetta Chimica Italiana; vol. 20; (1890); p. 639 View in Reaxys Gasiorowski; Wayss; Chemische Berichte; vol. 18; (1885); p. 337,1938 View in Reaxys

S

S

Sn

Br

Br

Br

diphenyl tin dibromide

Rx-ID: 8275387 View in Reaxys 483/513 Yield

Conditions & References Polis; Chemische Berichte; vol. 22; (1889); p. 2916 View in Reaxys Br

Br

Br

Br

HN

Br

O Br O

Br

H 2N

Rx-ID: 721377 View in Reaxys 484/513 Yield

Conditions & References Bender; Chemische Berichte; vol. 20; (1887); p. 2749 View in Reaxys Levy; Jedlicka; Justus Liebigs Annalen der Chemie; vol. 249; (1888); p. 86 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Br

Br

Br

Br

HN

Br Br

Br

H 2N

O

Rx-ID: 722139 View in Reaxys 485/513 Yield

Conditions & References Levy; Jedlicka; Justus Liebigs Annalen der Chemie; vol. 249; (1888); p. 86 View in Reaxys

Cl Al

Br

Cl

Br

Br

Cl

Rx-ID: 6416669 View in Reaxys 486/513 Yield

Conditions & References Leroy; Bulletin de la Societe Chimique de France; vol. <2> 48; (1887); p. 211 View in Reaxys Br

Cl

Br Al

Br

Cl

Br

Br

Br

Cl

Br Br

Br

Br

Br

Rx-ID: 7175821 View in Reaxys 487/513 Yield

Conditions & References Leroy; Bulletin de la Societe Chimique de France; vol. <2> 48; (1887); p. 211 View in Reaxys

Br

Br

Br

Br

Br

Rx-ID: 846662 View in Reaxys 488/513 Yield

Conditions & References Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

Br

Br

Br

Br

Br

Rx-ID: 846663 View in Reaxys 489/513 Yield

Conditions & References Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Br

Br

Br

Br

Br

Rx-ID: 846664 View in Reaxys 490/513 Yield

Conditions & References With aluminium trichloride Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

Br

Br Br

Br Br

Rx-ID: 847501 View in Reaxys 491/513 Yield

Conditions & References Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

benzenediazopiperidide

Br

Rx-ID: 6416685 View in Reaxys 492/513 Yield

Conditions & References With hydrogen bromide Wallach; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 242 View in Reaxys

Br

Br

Cl

Br

Br

Cl

Al

Cl

O

Br

asymm.diphenylethane

O

Rx-ID: 6726238 View in Reaxys 493/513 Yield

Conditions & References T= 50 °C Anschuetz; Justus Liebigs Annalen der Chemie; vol. 235; (1886); p. 163 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Si

Br

Br

Br

tris-silico-benzoyl-orthosilicic acid

Rx-ID: 7088982 View in Reaxys 494/513 Yield

Conditions & References Polis; Chemische Berichte; vol. 19; (1886); p. 1021; Chemische Berichte; vol. 18; (1885); p. 1542 View in Reaxys

Br

Br

I

Br

I

Rx-ID: 6416670 View in Reaxys 495/513 Yield

Conditions & References Schramm; Chemische Berichte; vol. 18; (1885); p. 607 View in Reaxys

O– Br

Br

Na +

Br

O

Rx-ID: 278728 View in Reaxys 496/513 Yield

Conditions & References T= 190 °C Balbiano; Gazzetta Chimica Italiana; vol. 11; (1881); p. 399 View in Reaxys

Br

Br

Br

ZnCl2

Rx-ID: 6416699 View in Reaxys 497/513 Yield

Conditions & References Schiaparelli; Gazzetta Chimica Italiana; vol. 11; (1881); p. 69; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1881); p. 539 View in Reaxys

Br As

Br

Br

Br

arsenic tribromoide

Br

Rx-ID: 7921397 View in Reaxys 498/513 Yield

Conditions & References La Coste; Michaelis; Justus Liebigs Annalen der Chemie; vol. 201; (1880); p. 212 View in Reaxys

As

Br

Br

Br

phenylarsinic acid-dibromide

O

Rx-ID: 7924738 View in Reaxys 499/513

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Yield

Conditions & References La Coste; Michaelis; Justus Liebigs Annalen der Chemie; vol. 201; (1880); p. 212 View in Reaxys

N

N

Br

Br

Rx-ID: 847115 View in Reaxys 500/513 Yield

Conditions & References Merz; Weith; Chemische Berichte; vol. 10; (1877); p. 756 View in Reaxys T= 220 - 240 °C Merz; Weith; Chemische Berichte; vol. 10; (1877); p. 756 View in Reaxys -1 (v2)

Br

Br

Br

N

N+

Br

natrium carbonate

Rx-ID: 7976902 View in Reaxys 501/513 Yield

Conditions & References Griess; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 89; Journal of the Chemical Society; vol. 20; (1867); p. 64 View in Reaxys Griess; Journal of the Chemical Society; vol. 20; (1867); p. 94; Journal fuer Praktische Chemie (Leipzig); vol. <1> 101; (1867); p. 91 View in Reaxys

benzenediazonium bromoplatinate

Br

Rx-ID: 6416683 View in Reaxys 502/513 Yield

Conditions & References With sodium carbonate Griess; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 89; Journal of the Chemical Society; vol. 20; (1867); p. 64 View in Reaxys

benzenediazonium-perbromide

Br

Rx-ID: 6416684 View in Reaxys 503/513 Yield

Conditions & References With sodium carbonate Griess; Justus Liebigs Annalen der Chemie; vol. 137; (1866); p. 89; Journal of the Chemical Society; vol. 20; (1867); p. 64 View in Reaxys

Br Br

PBr Br

HO

Br

Br

Rx-ID: 6416677 View in Reaxys 504/513 Yield

Conditions & References Riche; Justus Liebigs Annalen der Chemie; vol. 121; (1862); p. 359 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Br

Br

Br

Br

Br

Rx-ID: 6674792 View in Reaxys 505/513 Yield

Conditions & References Couper; Annales de Chimie (Cachan, France); vol. <3> 52; (1858); p. 309; Justus Liebigs Annalen der Chemie; vol. 104; (1857); p. 225 View in Reaxys

Cl

H

Br

HN

Br

H 2N Br

Br

Br Br

Br Br

Br

Br

Br Br

Rx-ID: 5810423 View in Reaxys 506/513 Yield

Conditions & References Chattaway; Journal of the Chemical Society; vol. 95; p. 1072 View in Reaxys -2 (v1)

O

Br

H

O

(v1)

HN

Cu 2+

Br

S O

copper

nitrogen

H 2N

O

Rx-ID: 6217293 View in Reaxys 507/513 Yield

Conditions & References Gattermann; Hoelzle; Chemische Berichte; vol. 25; p. 1075 View in Reaxys

Cl Si

Br

Rx-ID: 31253399 View in Reaxys 508/513 Yield

Conditions & References Reaction Steps: 2 1: Na / xylene 2: Br2 With Na, Br2 in xylene vol. Si: MVol.C; 113, page 316 - 320 View in Reaxys

(v1)

–Br

(v2)

Mg+

Br

Br

Rx-ID: 31256196 View in Reaxys 509/513 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether in diethyl ether

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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vol. Sn: Org.Verb.2; 1.1.2.11, page 339 - 345 View in Reaxys Cl B Br

Rx-ID: 31291845 View in Reaxys 510/513 Yield

Conditions & References Reaction Steps: 2 vol. B: B-Verb.9; 6.3.2, page 303 - 314 View in Reaxys

O B Br

Rx-ID: 31292012 View in Reaxys 511/513 Yield

Conditions & References Reaction Steps: 2 vol. B: B-Verb.9; 6.3.2, page 303 - 314 View in Reaxys

Br

Br

B Br

Rx-ID: 31292317 View in Reaxys 512/513 Yield

Conditions & References Reaction Steps: 2 vol. B: B-Verb.9; 6.3.2, page 303 - 314 View in Reaxys

Br

B O

Rx-ID: 31292659 View in Reaxys 513/513 Yield

Conditions & References Reaction Steps: 2 vol. B: B-Verb.9; 6.3.2, page 303 - 314 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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