toluene (PhMe) to (bromomethyl)benzene (BnBr) [Reaxys, Reactions (64); 2016-03-02]

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Br

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64 reactions in Reaxys

2016-03-02 02h:35m:22s (EST)

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Br

Rx-ID: 750416 View in Reaxys 1/64 Yield 100 %

Conditions & References With bromine in tetrachloromethane, Time= 1.5h, Ambient temperature Venkatachalapathy, Chockalingam; Pitchumani, Kasi; Tetrahedron; vol. 53; nb. 7; (1997); p. 2581 - 2584 View in Reaxys

100 %

With manganese(IV) oxide, bromine in dichloromethane, Time= 1h, T= 0 °C , Product distribution, Further Variations: Solvents, Temperatures, reaction time Jiang, Xuefeng; Shen, Meihua; Tang, Yu; Li, Chaozhong; Tetrahedron Letters; vol. 46; nb. 3; (2005); p. 487 - 489 View in Reaxys

100 %

With bromine, sodium t-butanolate in cyclohexane, Heating Montoro, Raul; Wirth, Thomas; Synthesis; nb. 9; (2005); p. 1473 - 1478; Art.No: C00505SS View in Reaxys

100 %

With manganese(IV) oxide, bromine in dichloromethane, Time= 0.166667h, T= 20 °C Mathew; Ravi; Unny; Sivaprasad; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 8; (2006); p. 699 - 705 View in Reaxys

98 %

With La(N,N'-propylene-bis-(2-aminobenzamide))Cl3, bromine in tetrachloromethane, Time= 5h, T= 25 °C , also ethyl benzene, other lanthanides, var. temp. and time, Mechanism Swamy; Kumar; Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry; vol. 35; nb. 6; (1996); p. 489 - 493 View in Reaxys

98 %

With bromine in tetrachloromethane, Solvent 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

95 %

With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one, silica gel, Time= 4h, UV-irradiation Gupta, Neeraj; Kad, Goverdhan L.; Singh, Vasundhara; Singh, Jasvinder; Synthetic Communications; vol. 37; nb.

19; (2007); p. 3421 - 3428 View in Reaxys

94 %

With hydrogen peroxide, bromine in dichloromethane, water, Time= 4h, Reflux, Reagent/catalyst Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 261 - 269 View in Reaxys

93 %

With TBBDA, dibenzoyl peroxide in ethyl acetate, Time= 1.5h, Reflux Ghorbani-Vaghei, Ramin; Chegini, Mohammad; Veisi, Hojat; Karimi-Tabar, Mehdi; Tetrahedron Letters; vol. 50; nb. 16; (2009); p. 1861 - 1865 View in Reaxys

93 %

With Li2MnO3, bromine, oxygen, Time= 0.2h, T= 25 °C , p= 760.051Torr , Photolysis Nishina, Yuta; Morita, Junya; Ohtani, Bunsho; RSC Advances; vol. 3; nb. 7; (2013); p. 2158 - 2162 View in Reaxys

92 %

With N-Bromosuccinimide in acetonitrile, Time= 0.416667h, T= 20 °C , Flow reactor, Irradiation

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Cantillo, David; De Frutos, Oscar; Rincon, Juan A.; Mateos, Carlos; Oliver Kappe; Journal of Organic Chemistry; vol. 79; nb. 1; (2014); p. 223 - 229 View in Reaxys 91 %

General Procedure for Electrochemical Bromination General procedure: A solution of 4-methoxy toluene (0.625 g, 5 mmol) in 25ml chloroform wastaken in a beaker-type undivided cell. A 25percent aqueous sodium bromide solution(50 ml) containing 5ml of 47percent HBr was added to it. Platinum electrodes (each of10 cm2 area) were placed in the upper layer of the aqueous phase. The organic phasealone was stirred with a magnetic stirrer at a rate of 40 rpm in such a way that theorganic layer did not touch the electrodes. The electrolysis was conducted galvanostaticallyat a current density of 30mA=cm2 until the quantity of charge indicated inTable 1 was passed at 15 C.After completion of electrolysis, the lower organic phase was separated,washed with 10percent sodium thiosulfate solution followed by water (225 ml), anddried with anhydrous Na2SO4.

The solvent was removed under reduced pressureto afford 1.46 g (86percent yield) of 3-bromo 4-methoxy benzylbromide as product.

With hydrogen bromide, sodium bromide in chloroform, water, T= 10 - 25 °C , Electrolysis Kulangiappar; Anbukulandainathan; Raju; Synthetic Communications; vol. 44; nb. 17; (2014); p. 2494 - 2502 View in Reaxys

87 %

With bromine in tetrachloromethane, Time= 1h, T= 50 °C , Irradiation Kodomari; Sakamoto; Yoshitomi; Bulletin of the Chemical Society of Japan; vol. 62; nb. 12; (1989); p. 4053 - 4054 View in Reaxys

87.5 %

With boron tribromide in tetrachloromethane, Time= 48h, T= 20 °C , Inert atmosphere Chen, Hongbiao; Shen, Litao; Lin, Yuanbin; Synthetic Communications; vol. 40; nb. 7; (2010); p. 998 - 1003 View in Reaxys

85 %

With sol-gel entrapped pyridinium hydrobromide perbromide in hexane, Time= 8h, T= 65 °C Levin, Yevgenia; Hamza, Khalil; Abu-Reziq, Raed; Blum, Jochanan; European Journal of Organic Chemistry; nb.

6; (2006); p. 1396 - 1399 View in Reaxys

82 %

Typical procedure for the halogenations of 1 or 6 with SiCl4/NXS General procedure: To a mixture of NXS and substrate (1 or 6) in CH3CN at room temperature was added SiCl4 and the mixture left to stir until TLC showed the disappearance of the starting material. The reaction was then poured onto H2O and the mixture extracted with CH2Cl2. The extracts were combined, dried over MgSO4 and evaporated. The residue was purified by recrystallization (pet. ether-Et2O, 3:1) to give pure 2b-2g, 3b, or by silica gel column chromatography (hexane-EtOAc 10:1 or 30:1) to give pure 2a,h,i, 3a-5 or 7-9, respectively With N-Bromosuccinimide, tetrachlorosilane in acetonitrile, Time= 6h, T= 20 °C , Wohl-Ziegler reaction Salama, Tarek A.; Novak, Zoltan; Tetrahedron Letters; vol. 52; nb. 31; (2011); p. 4026 - 4029 View in Reaxys

80 %

With bromine, anhydrous lanthanum acetate in tetrachloromethane, Time= 4h, T= 60 °C , Irradiation Ouertani, Mohsen; Girard, Pierre; Kagan, Henry B.; Bulletin de la Societe Chimique de France; vol. <2> 2; nb. 9-10; (1982); p. 327 - 328 View in Reaxys

80 %

General Description of the Microreactor Mediated Benzylic Bromination in Concentrated Solar Radiation General procedure: A CHCl3 solution of alkylbenzene (0.5 M) was placed in a syringe, and a CHCl3 solution of Br2 (0.6 M) was placed in another syringe wrapped with aluminium foil. The reaction streams were introduced to each of the inlets of the capillary microreactor through a 25 cm FEP tubing segment. The injection rates for toluene and Br2 varied but were equal for both solutions. Sunlight was focussed with a Fresnel lens, and solar tracking was conducted manually every 15 min. The results ofthe reaction were collected into a brown vial containing an aqueous solution of Na2S2O3. After extraction with additional CHCl3, the organic layer was analysed. The crude yield and selectivity were calculated through GC/MS or 1H NMR analysis. The mixtures were purified via column chromatography.

With bromine in chloroform, Time= 0.025h, T= 12 - 27 °C , Flow reactor, Irradiation, Green chemistry, Solvent, Wavelength, Reagent/catalyst, Temperature, Time

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Kim, Young Joon; Jeong, Myung Jin; Kim, Ji Eun; In, Insik; Park, Chan Pil; Australian Journal of Chemistry; vol. 68; nb. 11; (2015); p. 1653 - 1656 View in Reaxys 79 %

With hydrogen bromide, hydrogen peroxide in water, Time= 24h, T= 27 °C , Irradiation Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Tetrahedron; vol. 65; nb. 22; (2009); p. 4429 - 4439 View in Reaxys

78 %

With N-Bromosuccinimide, 2,2'-azobis(isobutyronitrile) in tetrachloromethane, Time= 2h, Heating, Bromination Acharya; Joshi; Pesticide Science; vol. 55; nb. 8; (1999); p. 850 - 856 View in Reaxys

78 %

Reaction procedure for visible-light-induced NBS-mediated radical bromination reaction of ethyl 6-methyl[1,3]dioxolo[4,5-g]quinoline-7-carboxylate (1) General procedure: A solution of 1 (2.6 g, 10 mmol) in CCl4 (45 mL) was heated with vigorous stirring until the solution boiled gently, and then was exposed to illumination with a 150-W tungsten lamp. Maintaining the reaction temperature, 0.534 g portions of 2.67 g (15 mmol) NBS were added to the mixture every 1.0 h. After the addition of NBS was complete, the resulting reaction mixture continued to reflux with illumination until practically full conversion was achieved (6 h) (TLC). On completion, the reaction was cooled to 10 °C, and the precipitated succinimide was filtered. The filtrate was evaporated under vacuum to dryness. The residue was subjected to column chromatography over silica gel (200–400 mesh) using hexane/ethyl acetate mixture as eluent (10:1, v/v) to give 2.53 g of 2 along with 0.58 g of byproduct 3 as white solid.

With N-Bromosuccinimide in tetrachloromethane, Time= 10h, Reflux, Irradiation Li, Yang; Research on Chemical Intermediates; vol. 41; nb. 7; (2015); p. 4977 - 4985 View in Reaxys

75 %

With NBSacc, 2,2'-azobis(isobutyronitrile) in tetrachloromethane, Time= 5h, Ambient temperature, Irradiation Sanchez, Eduardo I.; Fumarola, Martin J.; Journal of Organic Chemistry; vol. 47; nb. 8; (1982); p. 1588 - 1590 View in Reaxys

75%

With oxygen, 1,2-dibromomethane, Time= 6h, T= 20 °C Kawakami, Kazumitsu; Tsuda, Akihiko; Chemistry - An Asian Journal; vol. 7; nb. 10; (2012); p. 2240 - 2252 View in Reaxys

75 %

General procedure for benzylic bromination of arenes with TBCA General procedure: a solution of the arene (2.0 mmol) and TBCA (0.25 g, 0.68 mmol) in EtOAc (20 mL) was refluxed for 6 h with stirring. At the end of the reaction, the precipitated cyanuric acid was then separated by filtration and the filtrate was evaporated to dryness under reduced pressure. The residue was passed through a short chromatographic column (SiO2, eluted with 15:1 hexane–ethyl acetate) to give the purified products.

With TBCA in ethyl acetate, Time= 6h, Reflux, Green chemistry De Almeida, Leonardo S.; Esteves, Pierre M.; De Mattos, Marcio C.S.; Tetrahedron Letters; vol. 56; nb. 49; (2015); p. 6843 - 6845 View in Reaxys

72 %

With water, bromine in dichloromethane, Time= 3.5h, T= 20 °C , UV-irradiation Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; European Journal of Organic Chemistry; nb. 2; (2006); p. 483 - 488 View in Reaxys

62.3 %

With hydrogen bromide, hydrogen peroxide in water, T= 0 °C , Incandescent lamp light Ju, Jie; Li, Yu Jin; Gao, Jian Rong; Jia, Jian Hong; Han, Liang; Sheng, Wei Jian; Jia, Yi Xia; Chinese Chemical Letters; vol. 22; nb. 4; (2011); p. 382 - 384 View in Reaxys

61 %

With [2,5-Me2C6H3SO2N(Br)CH2]2, dibenzoyl peroxide in tetrachloromethane, Time= 1.5h, T= 77 °C , Bromination Ardeshir, Khazaei; Abbas, Shirdarreh; Synthetic Communications; vol. 29; nb. 23; (1999); p. 4079 - 4085

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View in Reaxys 59 %

With TMATB in benzene, T= 25 °C Ghiaci; Sedaghat; Ranjbari; Gil; Applied Catalysis A: General; vol. 384; nb. 1-2; (2010); p. 18 - 26 View in Reaxys With Ascaridole, bromine, T= 25 °C , unter Ausschluss von Licht Kharasch et al.; Journal of the American Chemical Society; vol. 59; (1937); p. 1405 View in Reaxys With tetrachloromethane, N-Bromosuccinimide, dibenzoyl peroxide Schmid; Karrer; Helvetica Chimica Acta; vol. 29; (1946); p. 573,580 View in Reaxys With tetrachloromethane, N-Bromosuccinimide, dimethyl 2,2'-azobis(isobutyrate) Ford; Waters; Journal of the Chemical Society; (1952); p. 2240,2245 View in Reaxys With propylene Carbonate, bromine, dibenzoyl peroxide Ross et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 4327,4329 View in Reaxys durch Bromierung im Licht Patent; Zelinsky, Schering-Kahlbaum A. G.; DE478084; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 335 View in Reaxys v. Konek; Loczka; Chemische Berichte; vol. 57; (1924); p. 679 View in Reaxys With bromine van der Laan; Chem. Zentralbl.; vol. 77; nb. I; (1906); p. 662 View in Reaxys Beilstein; Justus Liebigs Annalen der Chemie; vol. 143; (1867); p. 369 View in Reaxys With bromine, im direkten Sonnenlicht Schramm; Chemische Berichte; vol. 18; (1885); p. 607 View in Reaxys Grimaux; Lauth; Bulletin de la Societe Chimique de France; vol. <2> 7; (1867); p. 108 View in Reaxys beim Bromieren v. Halban; Gast; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 91; (1916); p.

595 View in Reaxys With propylene Carbonate, N-Bromosuccinimide, dibenzoyl peroxide Ross et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 4327,4329 View in Reaxys With tetrachloromethane, N-Bromosuccinimide, unter Beschuss mit energiereichen Elektronen Cox; Swallow; Chemistry and Industry (London, United Kingdom); (1956); p. 1277 View in Reaxys With N-Bromosuccinimide, 2,2'-azobis(isobutyronitrile) in tetrachloromethane Maier, Ludwig; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 53; nb. 1-4; (1990); p. 43 - 67

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View in Reaxys 66 % Spectr.

With hexabromo-1,3-cyclopentadiene in acetonitrile, Time= 160h, Heating Magen, Shulamit; Oren, Jakob; Fuchs, Benzion; Tetrahedron Letters; vol. 25; nb. 31; (1984); p. 3369 - 3372 View in Reaxys With N-Bromosuccinimide, Perbenzoic acid, Time= 3h, Heating Donxia, Li; Dexian, Wu; Yaozhong, Li; Huaming, Zhao; Tetrahedron; vol. 42; nb. 15; (1986); p. 4161 - 4168 View in Reaxys

86.0 % Chromat.

With N-bromo-S,S-diphenyl sulfoximine, dibenzoyl peroxide in benzene, Time= 5h, T= 80 °C Akasaka, Takeshi; Furukawa, Naomichi; Oae, Shigeru; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1257 - 1261 View in Reaxys With Diethyl 2-bromomalonate in benzene, T= 70 °C , Irradiation Truksa, Scott V.; Nibler, Alan; Schatz, Bruce S.; Krosley, Kevin W.; Gleicher, Gerald Jay; Journal of Organic Chemistry; vol. 57; nb. 10; (1992); p. 2967 - 2970 View in Reaxys With N-Bromosuccinimide in tetrachloromethane, initiator: benzoyl peroxide Ashcroft, Martyn R.; Bougeard, Peter; Bury, Adrian; Cooksey, Christopher J.; Johnson, Michael D.; Journal of Organometallic Chemistry; vol. 289; (1985); p. 403 - 416 View in Reaxys

98 % Chro- With bromine in water, Irradiation mat.

Shaw, Henry; Perlmutter, Howard D.; Gu, Chen; Arco, Susan D.; Quibuyen, Titos O.; Journal of Organic Chemistry; vol. 62; nb. 2; (1997); p. 236 - 237 View in Reaxys Bromierung bei klarem Sonnenlicht oder bei UV-Bestrahlung v. Konek; Loczka; Chemische Berichte; vol. 57; (1924); p. 679 View in Reaxys 75.4 % Chromat.

With N-bromo-S,S-diphenyl sulfoximine in dichloromethane, Time= 5h, T= 0 °C , Irradiation, heating or irradiation, other solvent, presence of radical initiator or radical scavenger; homolytic halogenation of toluene with N-halogenosulphoximides, Product distribution Akasaka, Takeshi; Furukawa, Naomichi; Oae, Shigeru; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1257 - 1261 View in Reaxys With N-Bromosuccinimide in benzene, T= 80 °C , Irradiation, Rate constant Dneprovskii, A. S.; Eliseenkov, E. V.; Journal of Organic Chemistry USSR (English Translation); vol. 23; nb. 4; (1987); p. 711 - 719; Zhurnal Organicheskoi Khimii; vol. 23; nb. 4; (1987); p. 788 - 797 View in Reaxys With N-Bromosuccinimide in benzene, Irradiation, relative rate const. to 3-trifluoromethyltoluene, 1-fluoro-2-phenylethane and 1,1,1-trifluoro-2-phenylethane, Product distribution Dneprovskii, A. S.; Eliseenkov, E. V.; Mil'tsov, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 18; (1982); p. 317 - 324; Zhurnal Organicheskoi Khimii; vol. 18; nb. 2; (1982); p. 365 - 373 View in Reaxys With bromine, anhydrous lanthanum acetate in tetrachloromethane, Time= 4h, T= 60 °C , Irradiation, Catalytic benzylic bromination of various alkylbenzenes. Other lanthanide derivatives (SmCl3, Sm2O3, La2(CO3)3, La(CF3CO2)3., Product distribution Ouertani, Mohsen; Girard, Pierre; Kagan, Henry B.; Bulletin de la Societe Chimique de France; vol. <2> 2; nb. 9-10; (1982); p. 327 - 328

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View in Reaxys With Diethyl 2-bromomalonate in benzene, T= 70 °C , Irradiation, k(rel), Rate constant Truksa, Scott V.; Nibler, Alan; Schatz, Bruce S.; Krosley, Kevin W.; Gleicher, Gerald Jay; Journal of Organic Chemistry; vol. 57; nb. 10; (1992); p. 2967 - 2970 View in Reaxys With perchloric acid, mercury(II) diacetate, N-bromoacetamide in water, acetic acid, Time= 72h, T= 35 °C , other temperatures, ΔH(excit), ΔS(excit), ΔE(excit), velocity constants, effect of var. substrate conc., NBA conc., HClO4 conc. and solvent composition, Kinetics, Mechanism, Thermodynamic data Pati, Subas C.; Pathy, H. P.; Dev, B. R.; Zeitschrift fuer Physikalische Chemie (Leipzig); vol. 268; nb. 2; (1987); p.

385 - 391 View in Reaxys With N-Bromosuccinimide in dichloromethane, T= 80 °C , Irradiation, photobromination of various substituted toluenes in various solvents and various temperatures, determination of Hammett equation, Mechanism Kim, Sung Soo; Choi, Seung Yong; Kang, Chul Hyun; Journal of the American Chemical Society; vol. 107; (1985); p. 4234 - 4237 View in Reaxys With bromine, T= 50 °C , Product distribution Zhang, Ben-Li; Pionnier, Sebastien; Journal of Physical Organic Chemistry; vol. 14; nb. 4; (2001); p. 239 - 246 View in Reaxys 95 % Chro- With bromine, silica gel in tetrachloromethane, Time= 0.166667h, T= 20 °C mat.

Ghiaci; Asghari; Bulletin of the Chemical Society of Japan; vol. 74; nb. 6; (2001); p. 1151 - 1152 View in Reaxys 35 % Chro- With N-Bromosuccinimide, 1,3-di-n-butyl-imidazolium tetrafluoroborate, Time= 0.0833333h, T= 28 - 35 °C mat.

Rajagopal; Jarikote; Lahoti; Daniel, Thomas; Srinivasan; Tetrahedron Letters; vol. 44; nb. 9; (2003); p. 1815 - 1817 View in Reaxys With N-Bromosuccinimide, zirconium tetrachloride in dichloromethane, Time= 24h, T= 20 °C Zhang, Yanhua; Shibatomi, Kazutaka; Yamamoto, Hisashi; Synlett; nb. 18; (2005); p. 2837 - 2842; Art.No: Y06405ST View in Reaxys With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate), sodium bromide in acetonitrile, Time= 42h, T= 20 °C , Product distribution, Further Variations: Reagents, reaction times Syvret, Robert G.; Butt, Kathleen M.; Nguyen, Tung P.; Bulleck, Victoria L.; Rieth, Ryan D.; Journal of Organic Chemistry; vol. 67; nb. 13; (2002); p. 4487 - 4493 View in Reaxys With N-Bromosuccinimide in acetonitrile, Time= 0.25h, T= 30 °C , UV-irradiation Chhattise, Prakash K.; Ramaswamy; Waghmode, Suresh B.; Tetrahedron Letters; vol. 49; nb. 1; (2008); p. 189 194 View in Reaxys 1 :The reaction of NBS and toluene in the presence of 5 mole percent ZrCI4 did not give the ring substituted product, but rather benzyl bromide almost exclusively. Table 5 shows some additional examples. The reaction also proceeds smoothly in the presence of FeCk or AICI3 with almost the same reactivity as that of ZrCU. Without wishing to be bound by any theory of interpretation, it is believed that this reaction may proceed by a radical mechanism. In fact, the reaction does not proceed at all in the presence of a radical inhibitor. EPO <DP n="30"/>Table 5 ZrCI4 Catalyzed Radical Bromination of Aromatic Compound by NBSa(5 mol percent), CH2CI2 (4 c See spectroscopic data for characterization.

With N-Bromosuccinimide, zirconium tetrachloride in dichloromethane, Time= 24h, T= 20 °C , Conversion of starting material

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Patent; UNIVERSITY OF CHICAGO; JAPAN SCIENCE AND TECHNOLOGY AGENCY; WO2007/27917; (2007); (A2) English View in Reaxys With bromine, Time= 0.83h, T= 36 °C , Irradiation, neat (no solvent) Jereb, Marjan; Zupan, Marko; Stavber, Stojan; Helvetica Chimica Acta; vol. 92; nb. 3; (2009); p. 555 - 566 View in Reaxys With N-Bromosuccinimide, Time= 3.33333h, T= 36 °C , Irradiation, neat (no solvent), Reactivity, Time Jereb, Marjan; Zupan, Marko; Stavber, Stojan; Helvetica Chimica Acta; vol. 92; nb. 3; (2009); p. 555 - 566 View in Reaxys With N-Bromosuccinimide, 2,2'-azobis(isobutyronitrile) in tetrachloromethane, Time= 7h, Reflux Bi, Nai-Min; Ren, Ming-Guang; Song, Qin-Hua; Synthetic Communications; vol. 40; nb. 17; (2010); p. 2617 - 2623 View in Reaxys With N-Bromosuccinimide, dibenzoyl peroxide in tetrachloromethane, Reflux Amsharov, Konstantin Yu.; Kabdulov, Mikhail A.; Jansen, Martin; European Journal of Organic Chemistry; nb. 36; (2009); p. 6328 - 6335 View in Reaxys With N-Bromosuccinimide in tetrachloromethane, Reflux Yang, Long; Gao, Fang; Liu, Jian; Zhong, Xiaolin; Li, Hongru; Zhang, Shengtao; Chemistry Letters; vol. 39; nb.

6; (2010); p. 582 - 583 View in Reaxys With N-Bromosuccinimide in tetrachloromethane, Reflux Yang, Long; Gao, Fang; Liu, Jian; Zhong, Xiaolin; Li, Hongru; Zhang, Shengtao; Journal of Fluorescence; vol.

21; nb. 2; (2011); p. 545 - 554 View in Reaxys With N-Bromosuccinimide, dibenzoyl peroxide in carbonic acid dimethyl ester, Time= 15h, T= 110 °C , Inert atmosphere Zhao, Xi; Ng, Wing Yan; Lau, Kai-Chung; Collis, Alana E. C.; Horvath, Istvan T.; Physical Chemistry Chemical Physics; vol. 14; nb. 11; (2012); p. 3909 - 3914 View in Reaxys 97.6 With hydrogen bromide, hydrogen peroxide, T= 25 °C , Irradiation, neat (no solvent) %Chromat.

Yu, Wu-Bin; Yu, Dong-Ping; Zheng, Ming-Ming; Shan, Shu-Ting; Li, Yu-Jin; Gao, Jian-Rong; Journal of Chemical Research; vol. 36; nb. 5; (2012); p. 258 - 260 View in Reaxys 88 %Chromat.

General procedure General procedure: To a solution of aromatic compound 1a-q (1 mmol) in CH3CN (6 mL) and H2O (0.5 mL) were added KBr (0.5 mmol) and Oxone (2.2 mmol), and the mixture was stirred at 45°C. After completion (monitored by TLC), the reaction mixture was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with saturated aqueous Na2S2O3 and brine, dried over anhydrous Na2SO4. Removal of the solvent under vacuum afforded the crude product, which was purified by column chromatography using hexane/ethyl acetate as eluent (20 - 80 : 1).

With Oxonereg;, potassium bromide in water, acetonitrile, T= 45 °C Yin, Lixia; Wu, Jingjing; Xiao, Juan; Cao, Song; Tetrahedron Letters; vol. 53; nb. 33; (2012); p. 4418 - 4421 View in Reaxys With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione, dibenzoyl peroxide in tetrachloromethane, Time= 4h, T= 20 80 °C , Wohl-Ziegler Bromination, Temperature, Solvent, Reagent/catalyst, Time Tsuchiya, Daisuke; Kawagoe, Yuhsuke; Moriyama, Katsuhiko; Togo, Hideo; Organic Letters; vol. 15; nb. 16; (2013); p. 4194 - 4197

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View in Reaxys With bromine, silica gel, acetic acid, Reflux, Reagent/catalyst, Time, Temperature Barton, Benita; Hlohloza, Nkululeko S.; McInnes, Sonia M.; Zeelie, Bernard; Organic Process Research and Development; vol. 7; nb. 4; (2003); p. 571 - 576 View in Reaxys With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione, 2,2'-azobis(isobutyronitrile) in acetonitrile, Time= 2h, T= 20 °C , Reflux, Reagent/catalyst, Solvent Tabata, Masayuki; Moriyama, Katsuhiko; Togo, Hideo; European Journal of Organic Chemistry; vol. 2014; nb. 16; (2014); p. 3402 - 3410 View in Reaxys 2H

2H

2H

2H

2H

2H

2H

2H 2H

2H

2H 2H

Br 2H

2H 2H

Rx-ID: 2019293 View in Reaxys 2/64 Yield 84 %

Conditions & References With N-bromosuccinmide, dibenzoyl peroxide in tetrachloromethane, Time= 0.666667h, Heating, Bromination Meddour, Abdelkrim; Courtieu, Jacques; Tetrahedron Asymmetry; vol. 11; nb. 17; (2000); p. 3635 - 3644 View in Reaxys

75 %

With N-bromosuccinmide Wierlacher, Stefan; Sander, Wolfram; Uu, Michael T. H.; Journal of the American Chemical Society; vol. 115; nb.

20; (1993); p. 8943 - 8953 View in Reaxys

55 %

With N-bromosuccinmide, 2,2'-azo-bisisobutyronitrile, Time= 0.5h, Heating, Irradiation Moreno-Manas, M.; Bassa, J.; Llado, N.; Pleixats, R.; Journal of Heterocyclic Chemistry; vol. 27; nb. 3; (1990); p.

673 - 678 View in Reaxys With N-bromosuccinmide in tetrachloromethane, Heating Bethell, Donald; Jenkins, Iwan L.; Quan, Peter M.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1985); p. 1789 - 1796 View in Reaxys With bromine, Irradiation Cowburn; Live; Fischman; Agosta; Journal of the American Chemical Society; vol. 105; nb. 25; (1983); p. 7435 7442 View in Reaxys With N-bromosuccinmide, meta-chloroperoxybenzoic acid in tetrachloromethane, Time= 1h, Heating Pedersen; FitzGerald; Journal of Pharmaceutical Sciences; vol. 74; nb. 2; (1985); p. 188 - 192 View in Reaxys With N-bromosuccinmide in tetrachloromethane Gruter, Gert-Jan M.; Van Baar, Ben L. M.; Gerrits, Tom J.; Akkerman, Otto S.; Bickelhaupt, Friedrich; Barkow, Anja; Kuck, Dietmar; Journal of the Chemical Society. Perkin Transactions 2; vol. 5; (1996); p. 925 - 932 View in Reaxys With N-bromosuccinmide in tetrachloromethane Lefebvre, Michelle D.; Dettmer, Christine M.; McSwain, Rachel L.; Xu, Chen; Davila, Jonathan R.; Composto, Russell J.; Nguyen, SonBinh T.; Shull, Kenneth R.; Macromolecules; vol. 38; nb. 25; (2005); p. 10494 - 10502

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View in Reaxys With N-bromosuccinmide, dibenzoyl peroxide in tetrachloromethane, Time= 2h, T= 90 °C Zhao, Hong; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 7; (2008); p. 293 - 296 View in Reaxys With N-bromosuccinmide, dibenzoyl peroxide in tetrachloromethane, T= 90 °C Zhang, Xi-Sha; Zhang, Yun-Fei; Li, Zhao-Wei; Luo, Fei-Xian; Shi, Zhang-Jie; Angewandte Chemie - International Edition; vol. 54; nb. 18; (2015); p. 5478 - 5482; Angew. Chem.; vol. 127; nb. 18; (2015); p. 5568 - 5572,5 View in Reaxys

Br

Br

Br

Br

Br

Br

Rx-ID: 10226738 View in Reaxys 3/64 Yield

Conditions & References With N-bromosuccinmide, aluminium trichloride in dichloromethane, Time= 22h, T= 20 °C , Product distribution, Further Variations: Reagents, Temperatures Zhang, Yanhua; Shibatomi, Kazutaka; Yamamoto, Hisashi; Synlett; nb. 18; (2005); p. 2837 - 2842; Art.No: Y06405ST View in Reaxys Toluene can be dibrominated and tribrominated in the presence of an excess amount of NBS. For example, as shown in Scheme 19, dibrominated toluene can be obtained as the major product using 6 EPO <DP n="31"/>equivalents of NBS1 AICI3 (5 mole percent), in CH2CI2 at room temperature for 22 hours. As shown in Scheme 20, tribrominated toluene can be obtained as the major product using 10 equivalents of NBS, ZrCI4 (5 mole percent), in CHaCI2 at reflux for 22 hours.

With N-bromosuccinmide, zirconium tetrachloride in dichloromethane, Time= 22h, Heating / reflux, Product distribution / selectivity Patent; UNIVERSITY OF CHICAGO; JAPAN SCIENCE AND TECHNOLOGY AGENCY; WO2007/27917; (2007); (A2) English View in Reaxys Toluene can be dibrominated and tribrominated in the presence of an excess amount of NBS. For example, as shown in Scheme 19, dibrominated toluene can be obtained as the major product using 6 EPO <DP n="31"/>equivalents of NBS1 AICI3 (5 mole percent), in CH2CI2 at room temperature for 22 hours. As shown in Scheme 20, tribrominated toluene can be obtained as the major product using 10 equivalents of NBS, ZrCI4 (5 mole percent), in CHaCI2 at reflux for 22 hours.

With N-bromosuccinmide, AlCl3, aluminium chloride in dichloromethane, Time= 22h, T= 20 °C , Product distribution / selectivity Patent; UNIVERSITY OF CHICAGO; JAPAN SCIENCE AND TECHNOLOGY AGENCY; WO2007/27917; (2007); (A2) English View in Reaxys

Br

Br

Br

Rx-ID: 3537607 View in Reaxys 4/64 Yield

Conditions & References

11 %, 86 % With bromine in dichloromethane, Time= 2h, Ambient temperature, Irradiation Itoh, Akichika; Masaki, Yukio; Synlett; nb. 12; (1997); p. 1450 - 1452 View in Reaxys

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86 %, 11 % With bromine in dichloromethane, Time= 2h, Ambient temperature, Irradiation Itoh, Akichika; Masaki, Yukio; Synlett; nb. 12; (1997); p. 1450 - 1452 View in Reaxys 81 %, 4 %

With hydrogen bromide, dihydrogen peroxide in water, Time= 10h, T= 20 °C , Irradiation Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Tetrahedron Letters; vol. 47; nb. 40; (2006); p.

7245 - 7247 View in Reaxys

81 %, 7 %

With hydrogen bromide, dihydrogen peroxide in water, Time= 24h, T= 27 °C , Irradiation Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Tetrahedron; vol. 65; nb. 22; (2009); p. 4429 - 4439 View in Reaxys

77 %, 3 %

With N-bromosuccinmide in water, Time= 27h, T= 25 °C , Wohl-Ziegler bromination Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Tetrahedron Letters; vol. 47; nb. 7; (2006); p. 1097 - 1099 View in Reaxys

72 %, 22 % With Sodium bromate, sodium hydrogensulfite in water, ethyl acetate, Time= 4h, T= 20 °C , Bromination Kikuchi, Daisuke; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 63; nb. 17; (1998); p.

6023 - 6026 View in Reaxys 70 %, 28 % With dihydrogen peroxide, bromine in dichloromethane, water, Time= 4h, Reflux Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene; Organic Process Research and Development; vol. 2; nb. 4; (1998); p. 261 - 269 View in Reaxys 76 % With NBSacc in tetrachloromethane, Time= 0.25h, Ambient temperature, Irradiation, var. time and other reaction conSpectr., 18 ditions, var. free-radical initiators, Product distribution % Spectr.

Sanchez, Eduardo I.; Fumarola, Martin J.; Journal of Organic Chemistry; vol. 47; nb. 8; (1982); p. 1588 - 1590 View in Reaxys With N-bromosuccinmide, Time= 9.5h, T= 36 °C , Irradiation, neat (no solvent) Jereb, Marjan; Zupan, Marko; Stavber, Stojan; Helvetica Chimica Acta; vol. 92; nb. 3; (2009); p. 555 - 566 View in Reaxys With bromine, (R)-bromo alcohol in dichloromethane, Time= 8h, Reflux, Acidic conditions Patil, Rajendra D.; Bhadra, Sukalyan; Adimurthy, Subbarayappa; Ranu, Brindaban C.; Synthetic Communications; vol. 40; nb. 19; (2010); p. 2922 - 2929 View in Reaxys 2H

2H 2H

2H

2H

Br

Rx-ID: 2010910 View in Reaxys 5/64 Yield

Conditions & References With N-bromosuccinmide, P-450 phase-transfer in tetrachloromethane, Time= 1h, T= 105 °C , Heating, Rate constant Hanzlik, Robert P.; Schaefer, Angela R.; Moon, Joseph B.; Judson, Charles M.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 4926 - 4930 View in Reaxys With N-bromosuccinmide in tetrachloromethane

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Gruter, Gert-Jan M.; Van Baar, Ben L. M.; Gerrits, Tom J.; Akkerman, Otto S.; Bickelhaupt, Friedrich; Barkow, Anja; Kuck, Dietmar; Journal of the Chemical Society. Perkin Transactions 2; vol. 5; (1996); p. 925 - 932 View in Reaxys 2H

2

H 2H

2H

Br 2

2

H

2H

H

2

2H 2H

H

Rx-ID: 2014360 View in Reaxys 6/64 Yield

Conditions & References With N-bromosuccinmide in tetrachloromethane, Time= 20h, Heating Guthrie, Robert D.; Shi, Buchang; Journal of the American Chemical Society; vol. 112; nb. 8; (1990); p. 3136 - 3139 View in Reaxys With N-bromosuccinmide in tetrachloromethane Gruter, Gert-Jan M.; Van Baar, Ben L. M.; Gerrits, Tom J.; Akkerman, Otto S.; Bickelhaupt, Friedrich; Barkow, Anja; Kuck, Dietmar; Journal of the Chemical Society. Perkin Transactions 2; vol. 5; (1996); p. 925 - 932 View in Reaxys

Br H 13C

H 13C

Rx-ID: 2082016 View in Reaxys 7/64 Yield

Conditions & References

64 %

With N-bromosuccinmide, 2,2'-azo-bisisobutyronitrile in tetrachloromethane, pentane, T= 85 °C Gugel, Hansjoerg; Zeller, Klaus-Peter; Wentrup, Curt; Chemische Berichte; vol. 116; nb. 8; (1983); p. 2775 - 2784 View in Reaxys

2H

2H

2H

2H

2H

2H

2H

2H

2H

Br 2H

2H

2H 2H

2H

Rx-ID: 1986796 View in Reaxys 8/64 Yield

Conditions & References With N-bromosuccinmide in tetrachloromethane, Time= 20h, Heating Guthrie, Robert D.; Shi, Buchang; Journal of the American Chemical Society; vol. 112; nb. 8; (1990); p. 3136 - 3139 View in Reaxys

2H

2H

Br

Br

Rx-ID: 1978986 View in Reaxys 9/64 Yield

Conditions & References With N-bromosuccinmide, P-450 phase-transfer in tetrachloromethane, Time= 1h, T= 105 °C , Heating, Rate constant Hanzlik, Robert P.; Schaefer, Angela R.; Moon, Joseph B.; Judson, Charles M.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 4926 - 4930 View in Reaxys

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2H

2H 2

2H

H

Br

2

H Br

Rx-ID: 2008979 View in Reaxys 10/64 Yield

Conditions & References With N-bromosuccinmide, P-450 phase-transfer in tetrachloromethane, Time= 1h, T= 105 °C , Heating, Rate constant Hanzlik, Robert P.; Schaefer, Angela R.; Moon, Joseph B.; Judson, Charles M.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 4926 - 4930 View in Reaxys

Br

Br

Br

Br

Br

Rx-ID: 5065669 View in Reaxys 11/64 Yield 5 %, 2 %

Conditions & References With Sodium bromate, sodium hydrogensulfite in water, acetonitrile, Time= 4h, T= 20 °C , Bromination Kikuchi, Daisuke; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 63; nb. 17; (1998); p.

6023 - 6026 View in Reaxys

Br Br

Br

Rx-ID: 3537606 View in Reaxys 12/64 Yield 33 %, 10 %, 67 %

Conditions & References With K10-montmorillonite clay, bromine in tetrachloromethane, Time= 1.5h, Ambient temperature Venkatachalapathy, Chockalingam; Pitchumani, Kasi; Tetrahedron; vol. 53; nb. 7; (1997); p. 2581 - 2584 View in Reaxys

67 %, 10 %, 33 %

With K10-montmorillonite clay, bromine in tetrachloromethane, Time= 1.5h, Ambient temperature Venkatachalapathy, Chockalingam; Pitchumani, Kasi; Tetrahedron; vol. 53; nb. 7; (1997); p. 2581 - 2584 View in Reaxys

43 %, 29 %, 20 %

With sodium peroxide, hydrogen bromide in acetic acid, Time= 2h, T= 78 - 80 °C Rudakova, N. I.; Erykalov, Yu. G.; Zharikova, S. M.; Dmitrieva, E. V.; Mataradze, M. S.; Russian Journal of General Chemistry; vol. 65; nb. 2.2; (1995); p. 271 - 272; Zhurnal Obshchei Khimii; vol. 65; nb. 2; (1995); p. 315 - 317 View in Reaxys

43 %, 20 %, 29 %

With sodium peroxide, hydrogen bromide in acetic acid, Time= 2h, T= 78 - 80 °C Rudakova, N. I.; Erykalov, Yu. G.; Zharikova, S. M.; Dmitrieva, E. V.; Mataradze, M. S.; Russian Journal of General Chemistry; vol. 65; nb. 2.2; (1995); p. 271 - 272; Zhurnal Obshchei Khimii; vol. 65; nb. 2; (1995); p. 315 - 317 View in Reaxys

29 %, 20 %, 36 %

With sodium peroxide, hydrogen bromide in acetic acid, Time= 2h, T= 78 - 80 °C Rudakova, N. I.; Erykalov, Yu. G.; Zharikova, S. M.; Dmitrieva, E. V.; Mataradze, M. S.; Russian Journal of General Chemistry; vol. 65; nb. 2.2; (1995); p. 271 - 272; Zhurnal Obshchei Khimii; vol. 65; nb. 2; (1995); p. 315 - 317 View in Reaxys

15 %

With hydrogen bromide, dihydrogen peroxide in water, Time= 24h, T= 20 °C , Darkness Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej; Tetrahedron; vol. 65; nb. 22; (2009); p. 4429 - 4439 View in Reaxys

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With 2-farnesylacetoxyethyltriethylammonium bromide in acetonitrile, Time= 24h, T= 0 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Yoshida, Masato; Mochizuki, Hideki; Kamigata, Nobumasa; Chemistry Letters; (1988); p. 2017 - 2020 View in Reaxys With 2-farnesylacetoxyethyltriethylammonium bromide in acetonitrile, Time= 24h, T= 0 °C , other temperature and reaction time, Product distribution Yoshida, Masato; Mochizuki, Hideki; Kamigata, Nobumasa; Chemistry Letters; (1988); p. 2017 - 2020 View in Reaxys With hydrogen bromide, sodium bromide in chloroform, water, T= 0 - 2 °C , Electrolysis Raju; Kulangiappar; Anbu Kulandainathan; Muthukumaran; Tetrahedron Letters; vol. 46; nb. 41; (2005); p. 7047 - 7050 View in Reaxys

O

OH

O

Br O

HO

Rx-ID: 9534399 View in Reaxys 13/64 Yield

Conditions & References

83 %

With hydrogen bromide, oxygen, bromide, anhydrous cobalt diacetate, Manganese (II) acetate, T= 75 °C , atmospheric pressure, Kinetics, Product distribution Partenheimer, Walt; Advanced Synthesis and Catalysis; vol. 346; nb. 2-3; (2004); p. 297 - 306 View in Reaxys

Br HO

O

Rx-ID: 10062652 View in Reaxys 14/64 Yield

Conditions & References

36 %, 47 % With sodium periodate, sulfuric acid, lithium bromide, Time= 24h, T= 65 °C Shaikh, Tanveer M.; Sudalai, Arumugam; Tetrahedron Letters; vol. 46; nb. 33; (2005); p. 5589 - 5592 View in Reaxys 2H

2H

Br 2H

2H

Rx-ID: 10293947 View in Reaxys 15/64 Yield

Conditions & References With N-bromosuccinmide, dibenzoyl peroxide in tetrachloromethane, Time= 4h, T= 80 °C Bialecki, Jason; Ruzicka, Josef; Attygalle, Athula B.; Journal of Mass Spectrometry; vol. 41; nb. 9; (2006); p. 1195 - 1204 View in Reaxys

Br

H

Br

O

Br

Rx-ID: 3537608 View in Reaxys 16/64 Yield

Conditions & References With Ce(IV) ammonium sulphate, sodium bromide in water, trifluoroacetic acid, Time= 24h, T= 25 °C , Yield given.

Further byproducts given. Yields of byproduct given

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Makhon'kov, D.I.; Cheprakov, A.V.; Rodkin, M.A.; Mil'chenko, A.Yu.; Beletskaya, I.P.; Journal of Organic Chemistry USSR (English Translation); vol. 22; (1986); p. 24 - 32; Zhurnal Organicheskoi Khimii; vol. 22; nb. 1; (1986); p.

30 - 39 View in Reaxys 2H

2H

2H

2H

2H

2H

Br

2H

Rx-ID: 2008977 View in Reaxys 17/64 Yield

Conditions & References With bromine in tetrachloromethane, Irradiation Paulsen, Hans; Roeben, Wolfgang; Heiker, Fred R.; Tetrahedron Letters; vol. 21; (1980); p. 3679 - 3680 View in Reaxys

Br 2H

2H

Rx-ID: 2056306 View in Reaxys 18/64 Yield

Conditions & References With N-bromosuccinmide Chao, Herbert S.-I.; Berchtold, Glenn A.; Journal of Organic Chemistry; vol. 46; nb. 6; (1981); p. 1191 - 1194 View in Reaxys With N-bromosuccinmide, dibenzoyl peroxide Novak, Predrag; Meic, Zlatko; Vikic-Topic, Drazen; Smrecki, Vilko; Plavec, Janez; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 54; nb. 2; (1998); p. 327 - 333 View in Reaxys

Br

H

Br

Br

Br

Br

O

Rx-ID: 36257144 View in Reaxys 19/64 Yield

Conditions & References With perchloric acid, ammonium metavanadate(V), hydrogen peroxide, potassium bromide in dichloromethane, water, Time= 24h, T= 25 °C , pH= 1, Reagent/catalyst, Time, Solvent, pH-value Galloni, Pierluca; Mancini, Marco; Floris, Barbara; Conte, Valeria; Dalton Transactions; vol. 42; nb. 33; (2013); p.

11963 - 11970 View in Reaxys

Br

O HO

Rx-ID: 750417 View in Reaxys 20/64 Yield

Conditions & References

14 %, 52 % With tert.-butylhydroperoxide, copper(ll) bromide in acetic anhydride, T= 80 °C Chaintreau, Alain; Adrian, Guy; Couturier, Daniel; Synthetic Communications; vol. 11; nb. 8; (1981); p. 669 - 672 View in Reaxys With hydrogen bromide, oxygen, T= 195 - 200 °C , Gasphase Barnett et al.; Industrial and Engineering Chemistry; vol. 41; (1949); p. 2612,2614 View in Reaxys

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With oxygen, sodium bromide, anhydrous cobalt diacetate, T= 64.9 °C , kinetic control and diffusion control, Rate constant Shcherbina, F. F.; J. Gen. Chem. USSR (Engl. Transl.); vol. 58; nb. 6; (1988); p. 1336 - 1340,1188 - 1192 View in Reaxys

O

OH

Br O O

Rx-ID: 2884266 View in Reaxys 21/64 Yield

Conditions & References

3 %, 20 %

With selenium(IV) oxide, lithium bromide, Time= 24h, Heating Bergman, Jan; Engman, Lars; Journal of Organic Chemistry; vol. 47; nb. 26; (1982); p. 5191 - 5196 View in Reaxys

Br

Br

Br

Br

Br

Rx-ID: 749750 View in Reaxys 22/64 Yield

Conditions & References T= 150 - 180 °C Hunter; Edgar; Journal of the American Chemical Society; vol. 54; (1932); p. 2025,2026 View in Reaxys T= 150 - 180 °C Hunter; Edgar; Journal of the American Chemical Society; vol. 54; (1932); p. 2025,2026 View in Reaxys Time= 5h, T= 20 °C , UV-irradiation Nishina, Yuta; Ohtani, Bunsho; Kikushima, Kotaro; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1663 - 1667 View in Reaxys

2H

2H

Br

Rx-ID: 4933360 View in Reaxys 23/64 Yield

Conditions & References With N-bromosuccinmide, dibenzoyl peroxide Novak, Predrag; Meic, Zlatko; Vikic-Topic, Drazen; Smrecki, Vilko; Plavec, Janez; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 54; nb. 2; (1998); p. 327 - 333 View in Reaxys

2H

2H

Br

Rx-ID: 4933361 View in Reaxys 24/64 Yield

Conditions & References With N-bromosuccinmide, dibenzoyl peroxide Novak, Predrag; Meic, Zlatko; Vikic-Topic, Drazen; Smrecki, Vilko; Plavec, Janez; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 54; nb. 2; (1998); p. 327 - 333

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View in Reaxys

Br

H

O

O

HO

HO

Rx-ID: 8832539 View in Reaxys 25/64 Yield

Conditions & References With air, ozone, anhydrous cobalt diacetate in acetic acid, T= 95 °C , Kinetics, Further Variations: Reagents Litvinova; Galstyan; Russian Journal of Applied Chemistry; vol. 73; nb. 11; (2000); p. 2002 - 2003 View in Reaxys

F

F

Br

F

F

F

Br

F

Rx-ID: 26479450 View in Reaxys 26/64 Yield

Conditions & References in neat (no solvent), Kinetics, decomposition on heating with toluene; Coomber, J. W.; Whittle, E.; Transactions of the Faraday Society; vol. 63; (1967); p. 608 - 619 ; (from Gmelin) View in Reaxys vol. C: MVol.D2; 4.2.3.5.1, page 311 - 311 ; (from Gmelin) View in Reaxys O N

Br

Br

HN O

Rx-ID: 750179 View in Reaxys 27/64 Yield

Conditions & References With tetrachloromethane Orazi; Meseri; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 37; (1949); p. 192,196; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 38; (1950); p. 5,9 View in Reaxys

Br

H HO

O

Rx-ID: 3537609 View in Reaxys 28/64 Yield

Conditions & References

66.8 %, 7.7 With air, hydrogen bromide, Time= 8h, Irradiation %, 25.5 % Nakada; Fukushi; Hirota; Bulletin of the Chemical Society of Japan; vol. 63; nb. 3; (1990); p. 944 - 946 View in Reaxys With air, hydrogen bromide, Time= 8h, Irradiation, reaction with other substrate and other bromide, other reaction conditions, Product distribution Nakada; Fukushi; Hirota; Bulletin of the Chemical Society of Japan; vol. 63; nb. 3; (1990); p. 944 - 946 View in Reaxys

Br

Br

Br

Rx-ID: 5818098 View in Reaxys 29/64

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Yield

Conditions & References T= 166 °C , im Dunkeln, Kinetics Anderson et al.; Journal of Chemical Physics; vol. 21; (1953); p. 1258,1267 View in Reaxys T= 82 - 132 °C , im Licht der Wellenlaenge 489 nm, Kinetics Anderson et al.; Journal of Chemical Physics; vol. 21; (1953); p. 1258,1267 View in Reaxys im direkten Sonnenlicht und anschl. Abkuehlen.Irradiation Schramm; Chemische Berichte; vol. 18; (1885); p. 607 View in Reaxys T= 100 °C van der Laan; Recueil des Travaux Chimiques des Pays-Bas; vol. 26; (1907); p. 39,45 View in Reaxys Holleman; Recueil des Travaux Chimiques des Pays-Bas; vol. 27; (1908); p. 437 Anm. View in Reaxys T= 25 °C , Einwirkung von zerstreutem Tageslicht van der Laan; Recueil des Travaux Chimiques des Pays-Bas; vol. 26; (1907); p. 39,45 View in Reaxys

Br

O

Br

Br

O

Rx-ID: 5818099 View in Reaxys 30/64 Yield

Conditions & References T= 25 °C , unter Zutritt von Luft und Ausschluss von Licht Kharasch et al.; Journal of the American Chemical Society; vol. 59; (1937); p. 1405 View in Reaxys Kharasch; White; Mayo; Journal of Organic Chemistry; vol. 3; (1938); p. 33,40 View in Reaxys

Br

H

Br

HO

O

Rx-ID: 3536785 View in Reaxys 31/64 Yield

Conditions & References

280 %

With air, Time= 10h, Irradiation Nakada; Fukushi; Hirota; Bulletin of the Chemical Society of Japan; vol. 63; nb. 3; (1990); p. 944 - 946 View in Reaxys

O F

O O S

F

O

O

N

S

F Br Br F

F

NE

F

O O S

O S

F

N

F

F

F

Br

Br

F

N F

Br

Rx-ID: 26708623 View in Reaxys 32/64 Yield

Conditions & References 75°C, 20 h Koshar,R.J.; Mitsch,R.A.; Journal of Organic Chemistry; vol. 38; (1973); p. 3358 - 3363 ; (from Gmelin)

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View in Reaxys 75°C, 20 h vol. F: PerFHalOrg.SVol.3; 6.2.3.2, page 121 - 136 ; (from Gmelin) View in Reaxys O O

O

O

Br

Br

N

Br

Br O

Rx-ID: 45650 View in Reaxys 33/64 Yield

Conditions & References T= 100 °C , Product distribution Ross et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 4327,4329 View in Reaxys

O

O

O

Cl

O

O

Br

Cl

Br

N

Br

Cl O

Cl

Br

O

Rx-ID: 45648 View in Reaxys 34/64 Yield

Conditions & References T= 100 °C , Product distribution Ross et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 4327,4329 View in Reaxys

O

O O

O

O

Br

O

N

O O

O

Br Br

Br

Rx-ID: 45649 View in Reaxys 35/64 Yield

Conditions & References T= 100 °C , Product distribution Ross et al.; Journal of the American Chemical Society; vol. 80; (1958); p. 4327,4329 View in Reaxys

O

H N

Br Br

Rx-ID: 750282 View in Reaxys 36/64 Yield

Conditions & References Park et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 2189,2192 View in Reaxys Park et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 2189,2192 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

19/26

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Br

bromoamide of/the/ chloroacetic acid

Br

Rx-ID: 5818104 View in Reaxys 37/64 Yield

Conditions & References Park et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 2189,2192 View in Reaxys

Br

bromoamide of/the/ dichloroacetic acid

Br

Rx-ID: 5818105 View in Reaxys 38/64 Yield

Conditions & References Park et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 2189,2192 View in Reaxys

Br

bromoamide of/the/ trichloroacetic acid

Br

Rx-ID: 5818106 View in Reaxys 39/64 Yield

Conditions & References Park et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 2189,2192 View in Reaxys

Br

bromoamide of/the/ trifluoroacetic acid

Br

Rx-ID: 5818107 View in Reaxys 40/64 Yield

Conditions & References Park et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 2189,2192 View in Reaxys

F H N

F

Br Br

F

Br O

Rx-ID: 749806 View in Reaxys 41/64 Yield

Conditions & References Park et al.; Journal of the American Chemical Society; vol. 74; (1952); p. 2189,2192 View in Reaxys

Cl

Cl

Cl

Cl

Cl

Cl

Br

Cl Cl

Cl

Rx-ID: 3537605 View in Reaxys 42/64 Yield

Conditions & References With 2,2'-azo-bisisobutyronitrile, trichloromonobromomethane, Time= 8h, T= 80 °C , reaction in the presence of ethylene oxide, Product distribution, Mechanism Dneprovskii, A. S.; Iz'yurov, A. L.; Boyarskii, V. P.; Eliseenkov, E. V.; Journal of Organic Chemistry USSR (English Translation); vol. 26; nb. 4; (1990); p. 701 - 704; Zhurnal Organicheskoi Khimii; vol. 26; nb. 4; (1990); p. 819 - 823 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

20/26

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Br

Br

H

Br

Br

Rx-ID: 5818100 View in Reaxys 43/64 Yield

Conditions & References T= 166 °C , im Dunkeln, Kinetics Anderson et al.; Journal of Chemical Physics; vol. 21; (1953); p. 1258,1267 View in Reaxys T= 82 - 132 °C , Kinetics Anderson et al.; Journal of Chemical Physics; vol. 21; (1953); p. 1258,1267 View in Reaxys

Br

Br

Br

Br

Br

Rx-ID: 5818110 View in Reaxys 44/64 Yield

Conditions & References im zerstreuten Licht Seelig; Journal fuer Praktische Chemie (Leipzig); vol. <2> 39; (1889); p. 175 View in Reaxys T= 25 °C , und 50grad und 75grad im Dunkeln, Product distribution van der Laan; Recueil des Travaux Chimiques des Pays-Bas; vol. 26; (1907); p. 39,45 View in Reaxys Holleman; Recueil des Travaux Chimiques des Pays-Bas; vol. 27; (1908); p. 437 Anm. View in Reaxys im Dunkeln Holleman; Recueil des Travaux Chimiques des Pays-Bas; vol. 33; (1914); p. 188 View in Reaxys O N

O

NH N

N N O

N Br

O

NH N

Br

NO2

O

O

N

N

O

Br

O

N

O

O

Rx-ID: 8427411 View in Reaxys 45/64 Yield

Conditions & References

52 %

Time= 24h, Heating, Product distribution, Mechanism 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

Br N

Br

O

Rx-ID: 121793 View in Reaxys 46/64 Yield

Conditions & References Bredt; Hof; Chemische Berichte; vol. 33; (1900); p. 23 View in Reaxys With benzene

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Putochin; Zhurnal Obshchei Khimii; vol. 15; (1945); p. 332,337; ; (1946); p. 3741 View in Reaxys O N

Br

Br

N Br

O

Rx-ID: 146472 View in Reaxys 47/64 Yield

Conditions & References Orazi; Meseri; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 38; (1950); p. 5,9 View in Reaxys With tetrachloromethane Orazi; Meseri; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 37; (1949); p. 192,196; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 38; (1950); p. 5,9 View in Reaxys

Br

Br

oxygen

H

O HO

Rx-ID: 5958017 View in Reaxys 48/64 Yield

Conditions & References T= 200 °C Patent; Shell Devel. Co.; US2421392; (1944) View in Reaxys Patent; Shell Devel. Co.; US2415800; (1945) View in Reaxys Barnett et al.; Industrial and Engineering Chemistry; vol. 41; (1949); p. 2612,2614 View in Reaxys Shell Devel. Co; ; (1947); p. 3128,5893 View in Reaxys

O O

N

N

N

N

N

O

O

O

O

NH

O

Br

O

NH

N

Br

Br

NO2

N

N

N

O

O

Rx-ID: 8427412 View in Reaxys 49/64 Yield

Conditions & References

33 %, 45 %, 49 %

Time= 24h, Heating, Product distribution, Mechanism 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 Br

ZnCl2

N

Br Br

O

Rx-ID: 5818108 View in Reaxys 50/64 Yield

Conditions & References T= 80 °C Schmidt; Helvetica Chimica Acta; vol. 29; (1946); p. 1144,1147, 1148 View in Reaxys

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22/26

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O Cl

Cl

Cl

Cl

Br

Br

N N Br

O

Rx-ID: 146471 View in Reaxys 51/64 Yield

Conditions & References Orazi et al.; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 40; (1952); p. 91,97 View in Reaxys Orazi; Meseri; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 37; (1949); p. 263,266; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 38; (1950); p. 5,10 View in Reaxys Orazi; Meseri; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 38; (1950); p. 5,9 View in Reaxys O

Cl

Cl

Cl

Cl

N

Br

Br

HN O

Rx-ID: 750178 View in Reaxys 52/64 Yield

Conditions & References Orazi et al.; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 40; (1952); p. 91,97 View in Reaxys Orazi; Meseri; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 37; (1949); p. 263,266; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 38; (1950); p. 5,10 View in Reaxys Orazi; Meseri; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 38; (1950); p. 5,9 View in Reaxys O Ag+

O

Br

O

O–

O

O

O O

Br Br

Br

Br

Rx-ID: 3537380 View in Reaxys 53/64 Yield

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

bromo-vapour

Br

Rx-ID: 5818103 View in Reaxys 54/64 Yield

Conditions & References Lauth; Grimaux; Bulletin de la Societe Chimique de France; vol. <2> 7; (1867); p. 109 View in Reaxys

F HO

F F

O

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23/26

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O

F F Br

O

Br

H

Br

F

O

O

O

Rx-ID: 3537452 View in Reaxys 55/64 Yield

Conditions & References

12 % Turnov., 52 % Turnov., 13 % Turnov., 3 % Turnov.

Cl

With cobalt acetate tetrahydrate, lithium bromide, Time= 24h, Ambient temperature, var. time, var. conc., insted of Co(Ac)3 Mn(Ac)3 was used, without halide, presence of water, Product distribution, Mechanism Makhon'kov, D. I.; Rodkin, M. A.; Beletskaya, I. P.; Journal of Organic Chemistry USSR (English Translation); vol.

21; nb. 8; (1985); p. 1445 - 1452; Zhurnal Organicheskoi Khimii; vol. 21; nb. 8; (1985); p. 1585 - 1592 View in Reaxys

alkali bromide

Cl

Br

alkali bromate

Rx-ID: 5818102 View in Reaxys 56/64 Yield

Conditions & References Zmaczynski; Chemische Berichte; vol. 59; (1926); p. 711 View in Reaxys

Br Br

Br

Br

Br Br

Br

Br Br

Br

Br

HBr

Br

Br

Br

Rx-ID: 7454305 View in Reaxys 57/64 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

Br

Br

Br Br Cl Br

Br

Cl

Br Br

Cl

Cl

Br

Cl

HBr

Br

Rx-ID: 8276536 View in Reaxys 58/64 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

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24/26

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O O Cl

Cl

Cl

Br

Br

O

N

O

Cl

O

O

Rx-ID: 77231 View in Reaxys 59/64 Yield

Conditions & References Schmid; Karrer; Helvetica Chimica Acta; vol. 29; (1946); p. 573,580 View in Reaxys O

Cl

Cl

Cl

Cl

Br

NH N Br

O

Rx-ID: 119904 View in Reaxys 60/64 Yield

Conditions & References Orazi; Meseri; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 37; (1949); p. 192,196; Anales de la Asociacion Quimica Argentina (1921-2001); vol. 38; (1950); p. 5,9 View in Reaxys

O

Br N

Br

O

Rx-ID: 121792 View in Reaxys 61/64 Yield

Conditions & References Putochin; Zhurnal Obshchei Khimii; vol. 15; (1945); p. 332,337; ; (1946); p. 3741 View in Reaxys

Br

Br

Br Br

Rx-ID: 5818109 View in Reaxys 62/64 Yield

Conditions & References nach Zusatz von kleinen Mengen verschiedener Metalle und Nichtmetallverbindungen Tronow; Perschina; Zhurnal Obshchei Khimii; vol. 24; (1954); p. 1608,1613, 1616; engl. Ausg. S. 1593, 1597,1599 View in Reaxys

Br

Br

phosphorus

Br

Br

Br

Rx-ID: 5818112 View in Reaxys 63/64 Yield

Conditions & References Product distribution van der Laan; Recueil des Travaux Chimiques des Pays-Bas; vol. 26; (1907); p. 39,45 View in Reaxys

Br

Br

Br

Br PBr Br

Br Br

Br

Br

Rx-ID: 5818111 View in Reaxys 64/64 Yield

Conditions & References Product distribution

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25/26

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van der Laan; Recueil des Travaux Chimiques des Pays-Bas; vol. 26; (1907); p. 39,45 View in Reaxys

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