Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Query Query Br

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328 reactions in Reaxys

2018-07-24 19h:08m:55s (UTC)

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='74-96-4') AND (IDE.INCHI='RDHPKYGYEGBMSE-UHFFFAOYSA-N') NOT (RX.RXRN=1209224))

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

Rx-ID: 208717 View in Reaxys 1/328 Yield

Conditions & References

60 %

With 2AlBr3*CBr4, T= 55 - 65 °C Akhrem, Irena S.; Orlinkov, Alexander V.; Afanas'eva, Lyudmila V.; Mysov, Evgenii I.; Vol'pin, Mark E.; Tetrahedron Letters; vol. 36; nb. 51; (1995); p. 9365 - 9368 View in Reaxys With sulfur trioxide, sodium bromide, T= 300 - 325 °C Patent; Ethyl Corp.; DE937888; (1952) View in Reaxys

60 % Turnov.

With 2AlBr3*CBr4 in various solvent(s), Time= 6h, T= 55 - 65 °C , p= 34200Torr Akhrem; Orlinkov; Afanas'eva; Vol'pin; Russian Chemical Bulletin; vol. 45; nb. 5; (1996); p. 1148 - 1153 View in Reaxys With bromine, T= 350 °C Zhou, Xiao-Ping; Yilmaz, Aysen; Yilmaz, Gurkan A.; Lorkovic, Ivan M.; Laverman, Leroy E.; Weiss, Michael; Sherman, Jeffrey H.; McFarland, Eric W.; Stucky, Galen D.; Ford, Peter C.; Chemical Communications; nb. 18; (2003); p. 2294 2295 View in Reaxys A : Part A. Part A. Ethane Bromination Reaction A mixture of ethane (6.0 ml/minute) and bromine (Br2 0.30 ml/hour) was passed into a reactor (glass tube, ID 0.38", heating zone length 4"), and was heated to 330° C. The effluent was analyzed by GC/MS. 100percent bromine conversion with 80percent bromoethane selectivity was obtained.

The by product with 20percent selectivity was 1,1-dibromoethane.

With bromine Patent; GRT, Inc.; The Regents of the University of California; US6465696; (2002); (B1) English View in Reaxys Patent; GRI, Inc.; The Regents of the University of California; US6465699; (2002); (B1) English View in Reaxys Patent; GRT, Inc.; The Regents of the University of California; US6486368; (2002); (B1) English View in Reaxys Patent; Zhou, Xiao Ping; Lorkovic, Ivan Marc; Sherman, Jeffrey H.; US2002/198416; (2002); (A1) English View in Reaxys With hydrogen bromide, oxygen, T= 536.84 °C , p= 760.051Torr , Flow reactor, Catalytic behavior, Reagent/catalyst, Temperature Zichittella, Guido; Puértolas, Begoña; Siol, Sebastian; Paunović, Vladimir; Mitchell, Sharon; Pérez-Ramírez, Javier; ChemCatChem; vol. 10; nb. 6; (2018); p. 1282 - 1290 View in Reaxys

OH

Br

Rx-ID: 193855 View in Reaxys 2/328 Yield 93 %

Conditions & References 34 :Ethanol and hydrobromic acid were reacted to prepare bromoethane. The steps are as follows: In a 500 ml flask, 270 g of 60percent hydrobromic acid and 40 g of protonic acid catalyst or ionic liquid were added, maintained the material temperature at about 30°C, while stirring. To the system, 120 g of 95percent ethanol was added, the reaction flask was sealed and placed in a water bath to stir the reaction. The temperature continues to rise to boiling state for 1 h. The reaction flask was fed to a rectification plant, bromoethane were separated from the system. The system temperature was raised to 45 ~ 46 degrees C to collect crude ethyl bromide. When the top temperature increases to 60 ° C, collection of ethyl bromide was stopped. The crude ethyl

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

bromide was washed twice with 10percent NaOH solution, and re-distilled to obtain the finished product. The results of the reactions of each group are shown in Table 2.

With 2-pyrrolidonium hydrogen sulfate, hydrogen bromide, Time= 2h, T= 20 °C , Sealed tube Patent; SHANGYU NHU BIOCHEMICAL INDUSTRY CO., LTD.; ZHEJIANG NHU PHARMACEUTICAL CO., LTD.; ZHEJIANG NHU SPECIAL MATERIALS CO., LTD.; TIAN, JINJIN; ZHEN, JIANFEI; ZENG, XIANMING; SHAN, GUOHONG; GUAN, MINXIA; (9 pag.); CN104672053; (2016); (B) Chinese View in Reaxys 87 %

With bromine, Time= 0.5h Baklan, V. F.; Khil'chevskii, A. N.; D'yakovskaya, V. M.; Sologub, L. S.; Kukhar, V. P.; Russian Journal of Organic Chemistry; vol. 29; nb. 3.1; (1993); p. 454 - 456; Zhurnal Organicheskoi Khimii; vol. 29; nb. 3; (1993); p. 542 - 545 View in Reaxys

83 %

With sulfuric acid, hydrogen bromide, T= 75 °C Yang; Lin; Li; Synthetic Communications; vol. 31; nb. 18; (2001); p. 2817 - 2822 View in Reaxys With hydrogen bromide, Pyridine hydrobromide, T= 120 - 150 °C Patent; Chem.Fabr.v.Heyden; DE624693; (1933); Fortschr. Teerfarbenfabr. Verw. Industriezweige; 22<1939>40 View in Reaxys With copper salt, sulfuric acid, potassium bromide Ribas-Marques; ; vol. 6; (1946); p. 661; ; (1947); p. 4769 View in Reaxys With phosphorus, phosphorous, bromine Tseng; Hou; ; vol. 2; p. 57; Chem. Zentralbl.; vol. 105; nb. II; (1934); p. 1606 View in Reaxys Goshorn; Degering; Proceedings of the Indiana Academy of Science; vol. 45; (1936); p. 143,144; Chem. Zentralbl.; vol. 108; nb. II; (1937); p. 4178 View in Reaxys With disulphur dibromide, sulfuric acid Patent; Davies; US2359828; (1941) View in Reaxys With bromine, sulfur, zuletzt bei Siedetemperatur Patent; Davies; US2359828; (1941) View in Reaxys With bromine, iron, unter Eiskuehlung und fogende Destillation Dangjan; Zhurnal Obshchei Khimii; vol. 11; p. 108; ; (1946); p. 3392,3393 View in Reaxys Dangjan; Zhurnal Obshchei Khimii; vol. 11; p. 108; ; (1941); p. 6565 View in Reaxys With bromine, aluminium, unter Eiskuehlung und fogende Destillation Dangjan; Zhurnal Obshchei Khimii; vol. 11; p. 108; ; (1946); p. 3392,3393 View in Reaxys Dangjan; Zhurnal Obshchei Khimii; vol. 11; p. 108; ; (1941); p. 6565 View in Reaxys With hydrogen bromide Norris; American Chemical Journal; vol. 38; (1907); p. 640 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Fournier; Bulletin de la Societe Chimique de France; vol. <3>35; (1906); p. 622 View in Reaxys With phosphorus tribromide Sachs; Chem. Zentralbl.; vol. 70; nb. I; (1899); p. 1066 View in Reaxys Galewski; Sobczyk; Molecular crystals and liquid crystals; vol. 88; nb. 1-4; (1982); p. 81 - 86 View in Reaxys With phosphorus tribromide, quantitativer Verlauf Walker; Johnson; Journal of the Chemical Society; vol. 87; (1905); p. 1592 View in Reaxys With vitriol oil, potassium bromide de Vrij; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1857); p. 441 View in Reaxys With pumice stone, sulfur dioxide, water, bromine Bodroux; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 160; (1915); p. 204 View in Reaxys With alkali bromide, sulfuric acid Holt; Journal of the Chemical Society; vol. 109; (1916); p. 1 View in Reaxys Weston, Frank Edwin; Journal of the Chemical Society, Transactions; vol. 107; (1915); p. 1489 - 1490 View in Reaxys With phosphorus tribromide, zur herstellung von 14C-haltigem Aethylbromid Tolbert et al.; Journal of Organic Chemistry; vol. 14; (1949); p. 525,528 View in Reaxys With bromine Loewig; Justus Liebigs Annalen der Chemie; vol. 3; (1832); p. 288 View in Reaxys Patent; Davies; US2359828; (1941) View in Reaxys With phosphorus, bromine Serullas; Annales de Chimie (Cachan, France); vol. <2>34; (1827); p. 100; Annales de Chimie (Cachan, France); vol. <2>35; (1827); p. 293 View in Reaxys With naphthalene, bromine Taboury; Bulletin de la Societe Chimique de France; vol. <4>9; (1911); p. 124 View in Reaxys Organic Syntheses 1; 6 <New York 1921> View in Reaxys With hydrogen sulfide, bromine Patent; Degussa; US2717911; (1952) View in Reaxys Patent; Degussa; DE960455; (1952) View in Reaxys 100 % Spectr.

With chloro-trimethyl-silane, lithium bromide in acetonitrile, Time= 12h, Heating

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Olah, George A.; Gupta, B. G. Balaram; Malhotra, Ripudaman; Narang, Subhash C.; Journal of Organic Chemistry; vol.

45; nb. 9; (1980); p. 1638 - 1639 View in Reaxys With sulfuric acid, potassium bromide, Bromination Mundhe; Journal of the Indian Chemical Society; vol. 76; nb. 5; (1999); p. 246 - 249 View in Reaxys With phosphorus tribromide, Cooling with ice Attygalle, Athula B.; Bialecki, Jason B.; Nishshanka, Upul; Weisbecker, Carl S.; Ruzicka, Josef; Journal of Mass Spectrometry; vol. 43; nb. 9; (2008); p. 1224 - 1234 View in Reaxys With phosphorus tribromide in dichloromethane, Time= 0.5h, Cooling with ice Yang, Dejun; Zhu, Yifei; Yang, Na; Jiang, Qiangqiang; Liu, Renhua; Advanced Synthesis and Catalysis; vol. 358; nb. 11; (2016); p. 1731 - 1735 View in Reaxys O Br

O O

O P O

O O

P O

O

O

O O

P

O

O

Br

O O

P O

O

Rx-ID: 42058092 View in Reaxys 3/328 Yield 3.8 g

Conditions & References Time= 0.166667h, T= 130 - 175 °C Pevzner; Russian Journal of General Chemistry; vol. 86; nb. 1; (2016); p. 62 - 67; Zh. Obshch. Khim.; vol. 86; nb. 1; (2016); p.

68 - 74,7 View in Reaxys O

O

O

P Br

O

P O

O

Br

Rx-ID: 40652595 View in Reaxys 4/328 Yield

Conditions & References T= 70 °C , Sealed tube, Michaelis-Arbuzov Synthesis, Temperature Fernández-Valle, María Encarnación; Martínez-Álvarez, Roberto; Molero-Vílchez, Dolores; Pardo, Zulay D.; Sáez-Barajas, Elena; Herrera, Antonio; Journal of Organic Chemistry; vol. 80; nb. 2; (2015); p. 799 - 805

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys O Br Br

OH O

Br

OH

HO

Br O

Rx-ID: 40804135 View in Reaxys 5/328 Yield

Conditions & References Stage 1: With lithium diisopropyl amide in tetrahydrofuran, T= 0 - 40 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 2h, T= 20 - 25 °C Zorin; Zaynashev; Chanysheva; Russian Journal of General Chemistry; vol. 85; nb. 6; (2015); p. 1382 - 1385; Zh. Obshch.

Khim.; vol. 85; nb. 6; (2015); p. 914 - 917,4 View in Reaxys

HO Br Br

O

O

Br

O

OH

OH

H

H H

O

Br

H

OH

O

OH

Rx-ID: 40804136 View in Reaxys 6/328 Yield

Conditions & References Stage 1: With lithium diisopropyl amide in tetrahydrofuran, T= 0 - 40 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 2h, T= 20 - 25 °C Zorin; Zaynashev; Chanysheva; Russian Journal of General Chemistry; vol. 85; nb. 6; (2015); p. 1382 - 1385; Zh. Obshch.

Khim.; vol. 85; nb. 6; (2015); p. 914 - 917,4 View in Reaxys

HO Br Br

O

O

O

OH

OH

Br

H

H Br H

H O

O OH

OH

Rx-ID: 40804137 View in Reaxys 7/328 Yield

Conditions & References Stage 1: With lithium diisopropyl amide in tetrahydrofuran, T= 0 - 40 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 2h, T= 20 - 25 °C Zorin; Zaynashev; Chanysheva; Russian Journal of General Chemistry; vol. 85; nb. 6; (2015); p. 1382 - 1385; Zh. Obshch.

Khim.; vol. 85; nb. 6; (2015); p. 914 - 917,4 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

OH Br Br

O

O Br

HO

HO

Br

OH

OH

O

O

Rx-ID: 40804138 View in Reaxys 8/328 Yield

Conditions & References Stage 1: With lithium diisopropyl amide in tetrahydrofuran, T= 0 - 40 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 2h, T= 20 - 25 °C Zorin; Zaynashev; Chanysheva; Russian Journal of General Chemistry; vol. 85; nb. 6; (2015); p. 1382 - 1385; Zh. Obshch.

Khim.; vol. 85; nb. 6; (2015); p. 914 - 917,4 View in Reaxys

Br

Br Br Br

Rx-ID: 36107930 View in Reaxys 9/328 Yield

Conditions & References 4 :IMPROVEMENT EXAMPLE 4 [0046] Referring to FIG 2, bromine is produced in fluo-solids reactor 1. The bromine vapor passes through line 3 to condenser 2 where most of the bromine, typically up to about 95percent, for example, may be is condensed. The uncondensed bromine vapor passes through line 5 to absorber 4 and is flowed against a counterflow of water. Clean gasses from the cross-flow are vented to the atmosphere through line 6. Water saturated with bromine forming an aqueous bromine saturated solution passes through line 8 to extractor 7. In extractor 7, the aqueous bromine saturated solution flows against a counterflow of ethane gas which strips all, or substantially all, of the bromine from the water. The ethane containing the stripped bromine passes through line 9 to brominator reactor 10. Liquid bromine from condenser 2 passes through line 11 to vaporizer 12 where the liquid bromine is vaporized and preheated before passing through line 13 to brominator reactor 10. Bromine and ethane in brominator reactor 10 react to form ethyl bromide, ethyl dibromide, ethyl tri bromide, and hydrogen bromide gasses.

These gasses exiting reactor 10 pass through line 15 to neutralizing reactor 14 where ethyl di-bromide, ethyl tri -bromide, and hydrogen bromide are neutralized with a suspension of magnesium hydroxide flowing through line 19 from reactor 18. Liquids from neutralizing reactor 14 pass through line 32 to fluo solids reactor 1. Gasses from neutralizing reactor 14 pass through line 20 to condenser 12 where the gasses are cooled.

With bromine in water, Flow reactor, Industrial scale Patent; SAJET DEVELOPMENT LLC; MILLER, Jorge; KLING MILLER, Luisa; WO2013/119230; (2013); (A1) English View in Reaxys

N

Br

N

N

Br

N

Rx-ID: 3310125 View in Reaxys 10/328 Yield

Conditions & References Snow, Arthur W.; Griffith, James R.; Journal of Fluorine Chemistry; vol. 15; (1980); p. 471 - 486 View in Reaxys Braun reaction Hosseini, Yaser; Rastgar, Saeed; Zerrin Heren; Orhan Bueyuekguengoer; Pesyan, Nader Noroozi; Journal of the Chinese Chemical Society; vol. 58; nb. 3; (2011); p. 309 - 318 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

N

F F

F

F F

F F F

O+

Br–

F F

F

N+

F

P– F F

F

F F

N

F

F

F F

F F

Br

P–

F

O

F

F F

F

F

F

F

N

N+

N

F

F F F

F

Rx-ID: 28129766 View in Reaxys 11/328 Yield

Conditions & References

93.2 %

9 :Example 91-Cyano-4-dimethylaminopyridinium tris(pentafluoroethyl)trifluorophosphate A mixture of 5.93 g (25.90 mmol) of 1-cyano-4-dimethylaminopyridinium bromide and 14.30 g (26.09 mmol) of triethyloxonium tris(pentafluoroethyl)trifluorophosphate from Example 1 is heated to 60° C. (temperature of the oil bath) and stirred for five hours under a nitrogen atmosphere. Volatile constituents are pumped off over the course of one hour under reduced pressure (7 Pa) at 50° C. (temperature of the oil bath), giving 14.32 g of a solid. The yield of 1-cyano-4-dimethylaminopyridinium tris(pentafluoroethyl)trifluorophosphate is 93.2percent, based on the 1-cyano-4-dimethylaminopyridinium bromide employed. The product is investigated by NMR spectroscopy.1H NMR spectrum, ppm: 3.34 s (2CH3), 6.99 d (CH), 7.03 d (CH), 8.04 d (CH), 8.20 d (CH); J3 H,H=8.2 Hz.19F NMR spectrum, ppm: -43.57 dm (PF), -79.60 m (CF3), -81.30 m (2CF3), -87.00 dm (PF2), -115.05 dm (CF2), -115.60 dm (2CF2); J1 P,F=889 Hz, J1 P,F=906 Hz, J2 P,F=81 Hz, J2 P,F=107 Hz. , Time= 5h, T= 60 °C Patent; Ignatyev, Nikolai (Mykola); Bissky, German; Willner, Helge; US2009/36628; (2009); (A1) English View in Reaxys N

F

F

F

F

F

S O

S O

N+

O+

N–

O

Br–

F O

N

F

F

F

Br

N O

F

S O

F

N

–

S

F N+

O

O

O N

Rx-ID: 28129767 View in Reaxys 12/328 Yield 98.2 %

Conditions & References 14 :Example 141-Cyano-4-dimethylaminopyridinium bis(trifluoromethylsulfonyl)imide A mixture of 5.22 g (22.89 mmol) of 1cyano-4-dimethylaminopyridinium bromide and 8.77 g (22.88 mmol) of triethyloxonium bis(trifluoromethylsulfonyl)imide from Example 3 is heated to 60° C. (temperature of the oil bath) and stirred for five hours under a nitrogen atmosphere. Volatile constituents are pumped off over the course of one hour under reduced pressure (7 Pa) at 50° C. (temperature of the oil bath), giving 14.32 g of a solid. The yield of 1-cyano-4-dimethylaminopyridinium bis(trifluoromethylsulfonyl)imide is 98.2percent, based on the 1-cyano-4-dimethylaminopyridinium bromide employed. The product is investigated by NMR spectroscopy.1H NMR spectrum, ppm: 3.34 s (2CH3), 6.99 d (CH), 7.03 d (CH), 8.04 d (CH), 8.19 d (CH); J3 H,H=8.2 Hz.19F NMR spectrum, ppm: -78.96 s. , Time= 5h, T= 60 °C Patent; Ignatyev, Nikolai (Mykola); Bissky, German; Willner, Helge; US2009/36628; (2009); (A1) English View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

O O

O

O

Br

Br

P

P

O

Rx-ID: 29106616 View in Reaxys 13/328 Yield

Conditions & References T= 70 °C , Arbuzov reaction Shkrob, Ilya A.; Kaminski, Michael D.; Mertz, Carol J.; Rickert, Paul G.; Derzon, Mark S.; Rahimian, Kamyar; Journal of the American Chemical Society; vol. 131; nb. 43; (2009); p. 15705 - 15710 View in Reaxys -1

F (v4)

F

B FF

Br O+

Rx-ID: 29189887 View in Reaxys 14/328 Yield

Conditions & References With bromide in water, Time= 0.666667h, Inert atmosphere D'Ulivo, Alessandro; Pagliano, Enea; Onor, Massimo; Pitzalis, Emanuela; Zamboni, Roberto; Analytical Chemistry; vol.

81; nb. 15; (2009); p. 6399 - 6406 View in Reaxys O

O O

P

P

Br N

O

O

O

Br

N

Rx-ID: 11042071 View in Reaxys 15/328 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 3h, T= 160 °C , Arbuzov reaction Singh, Anil K.; Asefa, Abera; Synthetic Communications; vol. 37; nb. 9; (2007); p. 1491 - 1494 View in Reaxys

O

O

Br

P O

O

Rx-ID: 25596032 View in Reaxys 16/328 Yield

Conditions & References 3; 4 :EXAMPLE 3Dealkylation of Phosphates with Salpen(tBu)(BBr2)2 Salpen(tBu)(BBr2)2, prepared as described in Example 1, was evaluated for its ability to dealkylate various phosphate esters. In a NMR tube, phosphate was added to an equimolar solution of Salpen(tBu)(BBr2)2 in CDCl3 and held at room temperature for 30 minutes. The reaction was monitored by 1H NMR. As shown in Table 1, significant dealkylation, measured by the amount of phosphate remaining in the reaction mixture in comparison to the amount of alkyl bromide produced, could be achieved with the composition of the present invention. TABLE 1 Percent dealkylation of phosphates with Salpen(tBu)(BBr2)2 PhosphateConversion (percent)a (MeO)3P(O) 89 (EtO)3P(O) 63 (nBuO)3P(O) 99 (nPentO)3P(O) 98 (MeO)2P(O)H 85 (MeO)2P(O)Me 99 (iPrO)2P(O)H 63 (PhO)2((2-Et)HexO)P(O) 71 (Me3SiO)3P(O) 98 (PhO)3P(O) 0 aThe percent conversion was determined by the amount of phosphate remaining to the amount of alkyl bromide produced in the 1H NMR.; EXAMPLE 4Dealkylation of Phosphates with Binuclear Boron CompoundsVarious

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

binuclear boron compounds, synthesized substantially as described in Examples 1 and 2, were evaluated for dealkylation of phosphate esters as described in Example 3. For comparison, a positive control consisting of BBr3 in CDCl3 was used. As shown in Tables 2-5, the compounds of the present invention were effective in cleaving phosphate bonds for various phosphate compounds. In contrast, BBr3 was ineffective (Table 5). Activity of the boron halide compounds of the present invention did not decrease with extension of the alkyl chain on the phosphates. However, a slight decrease in activity of the compounds was observed with the branched phosphates such as (PhO)2((2-Et)HexO)P(O). TABLE 2 Dealkylation of phosphates by Salen ligands having the formula L[BBr2]2. Phosphate (PhO)2P(O) (MeO)3P(O)(EtO)3P(O)(n-BuO)3P(O)(MeO)2P(O)Me (2-ethylhexyl)(MeSiO)3P(O) 30 24 30 24 30 24 30 24 30 24 30 24L[BBr2]2 min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. Salen(t) 76 94 26 32 42 57 61 77 48 58 88 89 Salpen(t) 74 82 68 74 99 99 84 99 75 83 98 98 Salben(t) 60 78 46 53 77 91 87 92 64 81 90 96 Salhen(t) 58 81 55 66 60 69 37 47 88 93 79 79 With Salpen(tBu)(BBr2)2 in chloroform-d1, Time= 0.5 - 24h, T= 20 °C , Conversion of starting material Patent; University of Kentucky Research Foundation; US7166591; (2007); (B1) English View in Reaxys 4 :EXAMPLE 4Dealkylation of Phosphates with Binuclear Boron CompoundsVarious binuclear boron compounds, synthesized substantially as described in Examples 1 and 2, were evaluated for dealkylation of phosphate esters as described in Example 3.

For comparison, a positive control consisting of BBr3 in CDCl3 was used. As shown in Tables 2-5, the compounds of the present invention were effective in cleaving phosphate bonds for various phosphate compounds. In contrast, BBr3 was ineffective (Table 5). Activity of the boron halide compounds of the present invention did not decrease with extension of the alkyl chain on the phosphates. However, a slight decrease in activity of the compounds was observed with the branched phosphates such as (PhO)2((2-Et)HexO)P(O).; TABLE 5 Dealkylation of phosphates by BBr3. Phosphate (PhO)2P(O) (MeO)3P(O)(EtO)3P(O)(nBuO)3P(O)(MeO)2P(O)H(MeO)2P(O)Me(i-PrO)2P(O)H (2-ethylhexyl)(MeSiO)3P(O) 30 24 30 24 30 24 30 24 30 24 30 24 30 24 30 24 min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. BBr3 1.1 3.4 0 2.7 5 0 1 12 2 2 0 0 0 7 11 20 BBromo 74 99 37 66 31 54 84 87 58 92 76 84 87 95 99 99 aB-Bromocatecholborane; EXAMPLE 3Dealkylation of Phosphates with Salpen(tBu)(BBr2)2 Salpen(tBu)(BBr2)2, prepared as described in Example 1, was evaluated for its ability to dealkylate various phosphate esters. In a NMR tube, phosphate was added to an equimolar solution of Salpen(tBu)(BBr2)2 in CDCl3 and held at room temperature for 30 minutes. The reaction was monitored by 1H NMR. As shown in Table 1, significant dealkylation, measured by the amount of phosphate remaining in the reaction mixture in comparison to the amount of alkyl bromide produced, could be achieved with the composition of the present invention.

With boron tribromide in chloroform-d1, Time= 0.5 - 24h, T= 20 °C , Conversion of starting material Patent; University of Kentucky Research Foundation; US7166591; (2007); (B1) English View in Reaxys 4 :EXAMPLE 4Dealkylation of Phosphates with Binuclear Boron CompoundsVarious binuclear boron compounds, synthesized substantially as described in Examples 1 and 2, were evaluated for dealkylation of phosphate esters as described in Example 3.

For comparison, a positive control consisting of BBr3 in CDCl3 was used. As shown in Tables 2-5, the compounds of the present invention were effective in cleaving phosphate bonds for various phosphate compounds. In contrast, BBr3 was ineffective (Table 5). Activity of the boron halide compounds of the present invention did not decrease with extension of the alkyl chain on the phosphates. However, a slight decrease in activity of the compounds was observed with the branched phosphates such as (PhO)2((2-Et)HexO)P(O).; TABLE 5 Dealkylation of phosphates by BBr3. Phosphate (PhO)2P(O) (MeO)3P(O)(EtO)3P(O)(nBuO)3P(O)(MeO)2P(O)H(MeO)2P(O)Me(i-PrO)2P(O)H (2-ethylhexyl)(MeSiO)3P(O) 30 24 30 24 30 24 30 24 30 24 30 24 30 24 30 24 min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. BBr3 1.1 3.4 0 2.7 5 0 1 12 2 2 0 0 0 7 11 20 BBromo 74 99 37 66 31 54 84 87 58 92 76 84 87 95 99 99 aB-Bromocatecholborane; EXAMPLE 3Dealkylation of Phosphates with Salpen(tBu)(BBr2)2 Salpen(tBu)(BBr2)2, prepared as described in Example 1, was evaluated for its ability to dealkylate various phosphate esters. In a NMR tube, phosphate was added to an equimolar solution of Salpen(tBu)(BBr2)2 in CDCl3 and held at room temperature for 30 minutes. The reaction was monitored by 1H NMR. As shown in Table 1, significant dealkylation, measured by the amount of phosphate remaining in the reaction mixture in comparison to the amount of alkyl bromide produced, could be achieved with the composition of the present invention.

With bromocatecholborane in chloroform-d1, Time= 0.5 - 24h, T= 20 °C , Conversion of starting material Patent; University of Kentucky Research Foundation; US7166591; (2007); (B1) English View in Reaxys 4 :Various binuclear boron compounds, synthesized substantially as described in Examples 1 and 2, were evaluated for dealkylation of phosphate esters as described in Example 3. For comparison, a positive control consisting of BBr3 in CDCl3 was used. As shown in Tables 2-5, the compounds of the present invention were effective in cleaving phosphate bonds for various phosphate

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

compounds. In contrast, BBr3 was ineffective (Table 5). Activity of the boron halide compounds of the present invention did not decrease with extension of the alkyl chain on the phosphates. However, a slight decrease in activity of the compounds was observed with the branched phosphates such as (PhO)2((2-Et)HexO)P(O). TABLE 2 Dealkylation of phosphates by Salen ligands having the formula L[BBr2]2. Phosphate (PhO)2P(O) (MeO)3P(O)(EtO)3P(O)(n-BuO)3P(O)(MeO)2P(O)Me (2-ethylhexyl)(MeSiO)3P(O) 30 24 30 24 30 24 30 24 30 24 30 24L[BBr2]2 min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. Salen(t) 76 94 26 32 42 57 61 77 48 58 88 89 Salpen(t) 74 82 68 74 99 99 84 99 75 83 98 98 Salben(t) 60 78 46 53 77 91 87 92 64 81 90 96 Salhen(t) 58 81 55 66 60 69 37 47 88 93 79 79; EXAMPLE 3Dealkylation of Phosphates with Salpen(tBu)(BBr2)2 Salpen(tBu)(BBr2)2, prepared as described in Example 1, was evaluated for its ability to dealkylate various phosphate esters. In a NMR tube, phosphate was added to an equimolar solution of Salpen(tBu)(BBr2)2 in CDCl3 and held at room temperature for 30 minutes. The reaction was monitored by 1H NMR. As shown in Table 1, significant dealkylation, measured by the amount of phosphate remaining in the reaction mixture in comparison to the amount of alkyl bromide produced, could be achieved with the composition of the present invention.

With salen(tBu)[BBr2]2 in chloroform-d1, Time= 0.5 - 24h, T= 20 °C , Conversion of starting material Patent; University of Kentucky Research Foundation; US7166591; (2007); (B1) English View in Reaxys 4 :Various binuclear boron compounds, synthesized substantially as described in Examples 1 and 2, were evaluated for dealkylation of phosphate esters as described in Example 3. For comparison, a positive control consisting of BBr3 in CDCl3 was used. As shown in Tables 2-5, the compounds of the present invention were effective in cleaving phosphate bonds for various phosphate compounds. In contrast, BBr3 was ineffective (Table 5). Activity of the boron halide compounds of the present invention did not decrease with extension of the alkyl chain on the phosphates. However, a slight decrease in activity of the compounds was observed with the branched phosphates such as (PhO)2((2-Et)HexO)P(O). TABLE 2 Dealkylation of phosphates by Salen ligands having the formula L[BBr2]2. Phosphate (PhO)2P(O) (MeO)3P(O)(EtO)3P(O)(n-BuO)3P(O)(MeO)2P(O)Me (2-ethylhexyl)(MeSiO)3P(O) 30 24 30 24 30 24 30 24 30 24 30 24L[BBr2]2 min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. Salen(t) 76 94 26 32 42 57 61 77 48 58 88 89 Salpen(t) 74 82 68 74 99 99 84 99 75 83 98 98 Salben(t) 60 78 46 53 77 91 87 92 64 81 90 96 Salhen(t) 58 81 55 66 60 69 37 47 88 93 79 79; EXAMPLE 3Dealkylation of Phosphates with Salpen(tBu)(BBr2)2 Salpen(tBu)(BBr2)2, prepared as described in Example 1, was evaluated for its ability to dealkylate various phosphate esters. In a NMR tube, phosphate was added to an equimolar solution of Salpen(tBu)(BBr2)2 in CDCl3 and held at room temperature for 30 minutes. The reaction was monitored by 1H NMR. As shown in Table 1, significant dealkylation, measured by the amount of phosphate remaining in the reaction mixture in comparison to the amount of alkyl bromide produced, could be achieved with the composition of the present invention.

With salhen(tBu)[BBr2]2 in chloroform-d1, Time= 0.5 - 24h, T= 20 °C , Conversion of starting material Patent; University of Kentucky Research Foundation; US7166591; (2007); (B1) English View in Reaxys 4 :Various binuclear boron compounds, synthesized substantially as described in Examples 1 and 2, were evaluated for dealkylation of phosphate esters as described in Example 3. For comparison, a positive control consisting of BBr3 in CDCl3 was used. As shown in Tables 2-5, the compounds of the present invention were effective in cleaving phosphate bonds for various phosphate compounds. In contrast, BBr3 was ineffective (Table 5). Activity of the boron halide compounds of the present invention did not decrease with extension of the alkyl chain on the phosphates. However, a slight decrease in activity of the compounds was observed with the branched phosphates such as (PhO)2((2-Et)HexO)P(O). TABLE 2 Dealkylation of phosphates by Salen ligands having the formula L[BBr2]2. Phosphate (PhO)2P(O) (MeO)3P(O)(EtO)3P(O)(n-BuO)3P(O)(MeO)2P(O)Me (2-ethylhexyl)(MeSiO)3P(O) 30 24 30 24 30 24 30 24 30 24 30 24L[BBr2]2 min. hr. min. hr. min. hr. min. hr. min. hr. min. hr. Salen(t) 76 94 26 32 42 57 61 77 48 58 88 89 Salpen(t) 74 82 68 74 99 99 84 99 75 83 98 98 Salben(t) 60 78 46 53 77 91 87 92 64 81 90 96 Salhen(t) 58 81 55 66 60 69 37 47 88 93 79 79; EXAMPLE 3Dealkylation of Phosphates with Salpen(tBu)(BBr2)2 Salpen(tBu)(BBr2)2, prepared as described in Example 1, was evaluated for its ability to dealkylate various phosphate esters. In a NMR tube, phosphate was added to an equimolar solution of Salpen(tBu)(BBr2)2 in CDCl3 and held at room temperature for 30 minutes. The reaction was monitored by 1H NMR. As shown in Table 1, significant dealkylation, measured by the amount of phosphate remaining in the reaction mixture in comparison to the amount of alkyl bromide produced, could be achieved with the composition of the present invention.

With (N,N'-butylenebis(3,5-di-tert-butyl(2-O)benzylidenimine)[BBr2]2 in chloroform-d1, Time= 0.5 - 24h, T= 20 °C , Conversion of starting material Patent; University of Kentucky Research Foundation; US7166591; (2007); (B1) English View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

O

Br

P

O

N

Br

O

O

P

O

N

S S

Rx-ID: 28644833 View in Reaxys 17/328 Yield

Conditions & References Meier, Herbert; Nicklas, Frank; Petermann, Ralf; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 62; nb. 12; (2007); p. 1525 - 1529 View in Reaxys O

O P O

Br

O

O Br

P

P O

O

O

O

Rx-ID: 10413296 View in Reaxys 18/328 Yield

Conditions & References

98 %

Time= 0.25h, T= 140 °C , microwave irradiation, Michaelis-Arbuzov reaction Vugts, Danielle J.; Koningstein, Manoe M.; Schmitz, Rob F.; De Kanter, Frans J. J.; Groen, Marinus B.; Orru, Romano V. A.; Chemistry - A European Journal; vol. 12; nb. 27; (2006); p. 7178 - 7189 View in Reaxys O

O P

O

Br

Br

O

P O

O

Rx-ID: 10429153 View in Reaxys 19/328 Yield

Conditions & References

94 %

Time= 0.0833333h, T= 180 °C , microwave irradiation, Michaelis-Arbuzov reaction Vugts, Danielle J.; Koningstein, Manoe M.; Schmitz, Rob F.; De Kanter, Frans J. J.; Groen, Marinus B.; Orru, Romano V. A.; Chemistry - A European Journal; vol. 12; nb. 27; (2006); p. 7178 - 7189 View in Reaxys

Br

Br

O Br

O

Br Br

P

Br

Br

O

O

P O

Br

OH

Rx-ID: 11101027 View in Reaxys 20/328 Yield

Conditions & References

15 %, 79 %, Time= 10h, T= 180 °C 37 % Gazizov; Karimova; Chernova; Pudovik; Sinyashin; Russian Journal of General Chemistry; vol. 76; nb. 7; (2006); p. 1170 1171 View in Reaxys

Br Br

Br

Br Br

Br Br

Br

Rx-ID: 24880283 View in Reaxys 21/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References 1 :A stream of ethane with a flow rate of 5 standard ml/min is passed through a bromine bubbler held at 21° C. The resulting mixture of ethane and bromine having a molar ratio of 3.6:1 (ethane:bromine) is passed through a glass reactor having a 3.6 mm inside diameter. The glass reactor is packed with borosilicate beads and the average residence time in the reactor is 27 s. 100percent of the bromine is converted. 24percent of the ethane is converted with selectivities of 86percent to ethyl bromide, 12percent to 1,2-dibromoethane, 1percent to 1,1-dibromoethane, and <1percent of 1,1,2-tribromoethane.

With bromine, Time= 0.0075h, T= 21 °C , Product distribution / selectivity Patent; Weiss, Michael J.; Sun, Shouli; US2006/229475; (2006); (A1) English View in Reaxys Br

O

O P O

Br

O O P

O

Br

O P

O O

Rx-ID: 23566642 View in Reaxys 22/328 Yield

Conditions & References 4 :A mixture consisting of 7.20 g of 1,2-bis(2-methylstyryl)naphthalene, 7.12 g of N-bromosuccinimide, 0.5 g of benzoyl peroxide containing 25percent water, and 80 ml of carbon tetrachloride was heated to reflux for 10 hours. After cooling, 200 ml of diethyl ether was added to the mixture and the deposited crystals were filtered off. The filtrate liquid was concentrated to obtain a bromomethyl substance. This bromomethyl substance was admixed with 13.29 g of triethyl phosphite and heated at 120° C. for 5 hours. After finishing the reaction, generated ethyl bromide and triethyl phosphite in excess were distilled off under the reduced pressure, to obtain tetraethyl 1,2-bis(2-methylstyryl)naphthalene-α,α'-diyl-diphosphonate. 1.82 g of benzophenone and 3.16 g of tetraethyl 1,2-bis(2-methylstyryl)naphthalene-α,α'-diyl-diphosphonate obtained in the above were dissolved in 30 ml of N,Ndimethylformamide. At 5 to 10° C., 1.30 g of potassium tert-butoxide was gradually added to the reaction over 10 minutes. The reaction mixture was then stirred at room temperature for 20 hours. 80 ml of ethanol and 25 ml of water were then added. The precipitate was recovered by filtration, washed with water and then dried to obtain yellow powders. The yellow powders were treated in the same way as in Example 1, to obtain compound No.1-02. , Time= 5h, T= 120 °C Patent; Matsushita Electric Industrial Co., Ltd.; US2005/96491; (2005); (A1) English View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

Br

O P

Br

O

O

P O O

Br

O

P O

O

Rx-ID: 23566643 View in Reaxys 23/328 Yield

Conditions & References 11 :A mixture consisting of 7.20 g of 2,3-bis(2-methylstyryl)naphthalene, 7.12 g of N-bromosuccinimide, 0.5 g of benzoyl peroxide containing 25percent water, and 80 ml of carbon tetrachloride was heated to reflux for 10 hours. After cooling, 200 ml of diethyl ether was added to the mixture and the deposited crystals were filtered off. The filtrate liquid was concentrated to obtain a bromomethyl substance. This bromomethyl substance was admixed with 13.29 g of triethyl phosphite and heated at 120° C. for 5 hours. After finishing the reaction, generated ethyl bromide and triethyl phosphite in excess were distilled off under the reduced pressure, to obtain tetraethyl 2,3-bis(2-methylstyryl)naphthalene-α,α'-diyl-diphosphonate. 1.82 g of benzophenone and 3.16 g of tetraethyl 2,3-bis(2-methylstyryl)naphthalene-α,α'-diyl-diphosphonate obtained in the above were dissolved in 30 ml of N,Ndimethylformamide. At 5 to 10° C., 1.30 g of potassium tert-butoxide was gradually added to the reaction over 10 minutes. The reaction mixture was then stirred at room temperature for 20 hours. 80 ml of ethanol and 25 ml of water were then added. The precipitate was recovered by filtration, washed with water and then dried to obtain pale yellow powders. The pale yellow powders were treated in the same way as in Example 8, to obtain compound No.1-22 , Time= 5h, T= 120 °C Patent; Matsushita Electric Industrial Co., Ltd.; US2005/96491; (2005); (A1) English View in Reaxys

O

O P O

Br

Br

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

O

O

P O

O

P O

O

Rx-ID: 23566644 View in Reaxys 24/328 Yield

Conditions & References 25 :A mixture consisting of 8.21 g of 9,10-bis(2-methylstyryl)anthracene, 7.12 g of N-bromosuccinimide, 0.5 g of benzoyl peroxide containing 25percent water, and 80 ml of carbon tetrachloride was heated to reflux for 10 hours. After cooling, 200 ml of diethyl ether was added to the mixture and the deposited crystals were filtered off. The filtrate liquid was concentrated to obtain a bromomethyl substance. This bromomethyl substance was admixed with 13.29 g of triethyl phosphite and heated at 120° C. for 5 hours. After finishing the reaction, generated ethyl bromide and triethyl phosphite in excess were distilled off under the reduced pressure, to obtain tetraethyl 9,10-bis(2-methylstyryl)anthracene-α,α'-diyl-diphosphonate. 1.82 g of benzophenone and 3.41 g of tetraethyl 9,10-bis(2-methylstyryl)anthracene-α,α'-diyl-diphosphonate obtained in the above were dissolved in 30 ml of N,Ndimethylformamide. At 5 to 10° C., 1.30 g of potassium tert-butoxide was gradually added to the reaction over 10 minutes. The reaction mixture was then stirred at room temperature for 20 hours. Ethanol was then added. The precipitate was recovered by filtration, washed with water and then dried to obtain yellow powders. The yellow powders were treated in the same way as in Example 22, to obtain compound No.1-62. , Time= 5h, T= 120 °C Patent; Matsushita Electric Industrial Co., Ltd.; US2005/96491; (2005); (A1) English View in Reaxys O

O P O

Br

Br

O P O

O

Br

P O

O O

Rx-ID: 23566645 View in Reaxys 25/328 Yield

Conditions & References 32 :A mixture consisting of 7.73 g of 4,4'-bis(2-methylstyryl)biphenyl, 7.12 g of N-bromosuccinimide, 0.5 g of benzoyl peroxide containing 25percent water, and 80 ml of carbon tetrachloride was heated to reflux for 10 hours. After cooling, 200 ml of diethyl ether was added to the mixture and the deposited crystals were filtered off. The filtrate liquid was concentrated to obtain a bromomethyl substance. This bromomethyl substance was admixed with 13.29 g of triethyl phosphite and heated at 120° C. for 5 hours. After finishing the reaction, generated ethyl bromide and triethyl phosphite in excess were distilled off under the reduced pressure, to obtain tetraethyl 4,4'-bis(2-methylstyryl)biphenyl-α,α'-diyl-diphosphonate. 1.82 g of benzophenone and 3.29 g of tetraethyl 4,4'-bis(2-methylstyryl)biphenyl-α,α'-diyl-diphosphonate obtained in the above were dissolved in 30 ml of N,N-dimethylformamide. At 5 to 10° C., 1.30 g of potassium tert-butoxide was gradually added to the reaction over 10 minutes. The reaction mixture was then stirred at room temperature for 20 hours. 80 ml of ethanol was then added. The precipitate was recovered

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

by filtration, washed with water and then dried to obtain pale yellow powders. The pale yellow powders were treated in the same way as in Example 29, to obtain compound No.1-82. , Time= 5h, T= 120 °C Patent; Matsushita Electric Industrial Co., Ltd.; US2005/96491; (2005); (A1) English View in Reaxys

Br

Br

O

O

P O

P O

O

O

Br

Rx-ID: 23585257 View in Reaxys 26/328 Yield

Conditions & References 18 :A mixture consisting of 8.21 g of 2,3-bis(2-methylstyryl)anthracene, 7.12 g of N-bromosuccinimide, 0.5 g of benzoyl peroxide containing 25percent water, and 80 ml of carbon tetrachloride was heated to reflux for 10 hours. After cooling, 200 ml of diethyl ether was added to the mixture and the deposited crystals were filtered off. The filtrate liquid was concentrated to obtain a bromomethyl substance. This bromomethyl substance was admixed with 13.29 g of triethyl phosphite and heated at 120° C. for 5 hours. After finishing the reaction, generated ethyl bromide and triethyl phosphite in excess were distilled off under the reduced pressure, to obtain tetraethyl 2,3-bis(2-methylstyryl)anthracene-α,α'-diyl-diphosphonate. 1.82 g of benzophenone and 3.41 g of tetraethyl 2,3-bis(2-methylstyryl)anthracene-α,α'-diyl-diphosphonate obtained in the above were dissolved in 30 ml of N,N-dimethylformamide. At 5 to 10° C., 1.30 g of potassium tert-butoxide was gradually added to the reaction over 10 minutes. The reaction mixture was then stirred at room temperature for. 20 hours. 80 ml of ethanol was then added. The precipitate was recovered by filtration, washed with water and then dried to obtain yellowish brown powders. The yellowish brown powders were treated in the same way as in Example 15, to obtain compound No.1-42.

With triethyl phosphite, Time= 5h, T= 120 °C Patent; Matsushita Electric Industrial Co., Ltd.; US2005/96491; (2005); (A1) English View in Reaxys Br

Rx-ID: 6395477 View in Reaxys 27/328 Yield 95.4%

Conditions & References 23.c : (c) (c) Preparation of phosphonate compound of formula (a)

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

To triethyl phosphite (34.7 g, 0.209 mol) was added dropwise over 1 hour at 70° C. the bromoacetic acid ester (50 g, 0.209 mol) obtained in the above step (b).

Then, the reaction mixture was slowly heated to 170° C., and the resulting ethyl bromide was removed by distillation.

After heating at that temperature for 16 hours, the reaction solution was distilled in vacuo to afford compound (a) (59.1 g; 95.4percent) as colorless oil with b.p. 141°-145° C. at 2 mmHg. Patent; Meiji Seika Kaisha, Ltd.; US4536336; (1985); (A) English View in Reaxys With ethanol, sulfuric acid, Methamphetamin, sulfur dioxide, bromine, und Destillieren langsam Kamm; Marvel; View in Reaxys Kamm; Marvel; Journal of the American Chemical Society; vol. 42; (1920); p. 307 View in Reaxys Jung,M.E.; Hatfield,G.L.; Tetrahedron Letters; (1978); p. 4483 - 4486 View in Reaxys Otsuki; Bulletin of the Chemical Society of Japan; vol. 49; (1976); p. 3713 View in Reaxys Tokura et al.; Bulletin of the Chemical Society of Japan; vol. 33; (1960); p. 1176 View in Reaxys Hudson; Kelsall; Journal of the Chemical Society [Section] B: Physical Organic; (1967); p. 390 View in Reaxys Davis et al.; Journal of Organic Chemistry; vol. 30; (1965); p. 415,416 View in Reaxys Lure et al.; Pharmaceutical Chemistry Journal; vol. 6; nb. 8; (1972); p. 518; Khimiko-Farmatsevticheskii Zhurnal; vol. 6; nb. 8; (1972); p. 29 View in Reaxys Urata et al.; Nippon Kagaku Zasshi; vol. 81; (1960); p. 1121; ; nb. 303; (1962) View in Reaxys Kirmse; Graf v. Wedel; Justus Liebigs Annalen der Chemie; vol. 666; (1963); p. 1,6,9 View in Reaxys Silbertson; Tomlinson; Canadian Journal of Chemistry; vol. 39; (1961); p. 706,709 View in Reaxys Fettis et al.; Journal of the Chemical Society; (1960); p. 4177,4182 View in Reaxys Ol'dekop et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 48; (1978); p. 1591,1456 View in Reaxys Schrumpf; Klein; Chemische Berichte; vol. 106; (1973); p. 266,278 View in Reaxys Anderson Jr.; Freenor; Journal of Organic Chemistry; vol. 37; (1972); p. 626 View in Reaxys Schmall; Schunack; Scientia Pharmaceutica; vol. 42; nb. 4; (1974); p. 248 - 255 View in Reaxys Guseinow et al.; Azerbaidzhanskii Khimicheskii Zhurnal; vol. 1; (1969); p. 50; ; vol. 71; nb. 90709; (1969) View in Reaxys Ponde; Trampe; Journal of Organic Chemistry; vol. 35; (1970); p. 1169 View in Reaxys Krasil'nikova et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 47; (1977); p. 2489,2275,2276,2277 View in Reaxys Kursanov et al.; Journal of Organic Chemistry USSR (English Translation); vol. 3; (1967); p. 1022; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 1060 View in Reaxys Higgins; Baldwin; Journal of Organic Chemistry; vol. 33; (1968); p. 1065 View in Reaxys Russell; Lamson; Journal of the American Chemical Society; vol. 91; (1969); p. 3967 View in Reaxys 24 : Alkylating agent: Ethyl bromide Alkylating agent: Ethyl bromide Chromatography eluant: 0percent to 1percent ether in petroleum ether.

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

13C NMR α 148.2, 140.7, 134.8, 123.0, 117.7, 111.0, 83.3, 81.4, 80.4, 72.0, 71.8, 71.7, 67.4, 63.8, 55.9, 51.4, 45.8, 45.4, 44.6, 40.3, 39.3, 29.1, 28.7, 26.4, 25.9, 25.7, 25.6, 25.3, 23.3, 21.8, 18.1, 18.0, 17.4, 15.0, 13.9, 12.4, 7.6, 2.5, -4.4, -4.9, -5.0, -5.3

Patent; Leo Pharmaceutical Products Ltd., A/S; US6573255; (2003); (B1) English View in Reaxys 29 : Alkylating agent: Ethyl bromide Alkylating agent: Ethyl bromide Chromatography eluant: 0percent to 2percent ether in petroleum ether.

13C NMR α 148.2, 140.8, 134.8, 123.0, 117.7, 111.0, 83.1, 81.4, 80.1, 72.9, 71.9, 71.8, 67.4, 63.8, 55.9, 51.4, 45.8, 45.4, 44.6, 40.4, 39.4, 28.7, 28.0, 27.2, 26.5, 25.8, 25.7, 25.6, 23.3, 21.8, 18.0, 18.0, 17.9, 17.7, 15.0, 13.9, 12.4, 8.3, 2.4, -4.4, -4.9, -4.9, -5.0, -5.3 Patent; Leo Pharmaceutical Products Ltd., A/S; US6573255; (2003); (B1) English View in Reaxys 32 : Alkylating agent: Ethyl bromide Alkylating agent: Ethyl bromide Chromatography eluant: 1percent ether in petroleum ether.

13C NMR α 148.2, 140.7, 134.8, 123.0, 117.7, 111.0, 83.4, 81.4, 80.4, 72.0, 71.8, 71.7, 67.8, 67.4, 63.8, 55.9, 51.3, 45.8, 45.4, 44.6, 40.3, 39.3, 29.0, 28.7, 26.3, 25.8, 25.7, 25.6, 25.4, 25.3, 23.3, 21.8, 18.0, 18.0, 17.4, 15.0, 14.0, 12.4, 7.6, 2.5, -4.4, -4.9 -5.0, -5.3 Patent; Leo Pharmaceutical Products Ltd., A/S; US6573255; (2003); (B1) English View in Reaxys 38 : Alkylating agent: Ethyl bromide Alkylating agent: Ethyl bromide Chromatography eluant: 0percent to 2percent ether in petroleum ether.

1H NMR α 6.22 (d,1H), 6.00 (d,1H), 5.17 (d,1H), 4.85 (d,1H), 4.36 (m,1H), 4.30 (q,1H), 4.20 (d,1H), 4.16 (m,1H), 3.72 (m,1H), 3.30 (m,1H), 2.82 (dd,1H), 2.43 (dd,1H), 2.20 (dd,1H), 1.99 (t,1H), 2.0-0.8 (m,15H), 1.44 (s,3H), 1.40 (s,3H), 1.26 (d,3H), 1.18 (t,3H), 1.07 (t,3H), 1.00 (d,3H), 0.87 (s,18H), 0.51 (s,3H), 0.05 (s,12H) Patent; Leo Pharmaceutical Products Ltd., A/S; US6573255; (2003); (B1) English View in Reaxys 41 : Alkylating agent: Ethyl bromide Alkylating agent: Ethyl bromide Chromatography eluant: 0percent to 2percent ether in petroleum ether.

13C NMR α 148.1, 140.7, 134.9, 122.9, 117.8, 111.0, 108.1, 86.5, 84.2, 81.3, 78.5, 71.9, 71.8, 67.3, 63.9, 55.9, 51.4, 45.9, 44.6, 40.2, 39.3, 31.4, 28.7, 27.5, 26.9, 26.3, 25.7, 25.6, 23.3, 21.8, 18.0, 18.0, 15.8, 15.0, 14.0, 12.4, 8.8, -4.9, -5.0, -5.3 Patent; Leo Pharmaceutical Products Ltd., A/S; US6573255; (2003); (B1) English View in Reaxys 57 : Alkylating agent: Ethyl bromide Alkylating agent: Ethyl bromide Chromatography eluant: 0percent to 10percent ether in petroleum ether.

13C NMR α 148.1, 140.6, 134.9, 122.9, 117.8, 111.0, 93.4, 82.6, 80.5, 74.3, 71.9, 67.3, 64.0, 55.8, 51.3, 45.9, 45.4, 40.1, 39.3, 28.7, 27.8, 25.7, 25.6, 25.0, 23.3, 21.8, 18.0, 17.9, 14.7, 14.0, 12.4, 7.2, 2.2, -4.9, -5.0, -5.3 Patent; Leo Pharmaceutical Products Ltd., A/S; US6573255; (2003); (B1) English View in Reaxys 20.a.25.a.b : b) b) Synthesis of the corresponding diethoxyphosphine oxides Example 1b Under a stream of nitrogen, 61 g of 1-bromo-2,4-dibutoxybenzene (0.20 mol) are heated together with 2.50 g of nickel(II) chloride (0.019 mol) to 160° C., and 46.3 g of triethyl phosphite (0.278 mol) are added dropwise over the course of 1 1/2 hours.

The ethyl bromide formed in this process is distilled off from the reaction mixture continuously.

After addition is complete, the mixture is stirred at 160° C. for 1 hour.

The reaction mixture is then cooled to room temperature, 50 ml of diethyl ether are added, the mixture is filtered through kieselguhr and the solvent is removed completely by concentration.

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Patent; Ciba Specialty Chemicals Corporation; US5965776; (1999); (A) English View in Reaxys The compound of thus formula (7) includes, for example, the following compounds: methyl chloride, ethyl bromide, methyl iodide, methyl methanesulfonate, methyl p-toluenesulfonate, and dimethylsulfuric acid.

Patent; Sumitomo Chemical Company, Limited; US6034128; (2000); (A) English View in Reaxys 8.a : EXAMPLE 8 65 g of 2-bromobenzothiophene (GC purity 92percent; 0.280 mol) were added to 1.5 g of palladium chloride (0.084 mol) at 25° C. under argon and while stirring well in a 50 ml four-necked sulphonation flask having a 10 cm Vigreux distillation headpiece, magnetic stirrer, thermometer, 50 ml dropping funnel with pressure compensation and headpiece for argon gasification.

After heating to 160° C. 61 g of triethyl phosphite (0.367 mol) were added dropwise to this mixture within 2 h.

The ethyl bromide formed was distilled off continuously in a dry ice receiver.

Patent; Hoffmann-La Roche Inc.; US6162929; (2000); (A) English View in Reaxys C.iv : N-2-Methylphenyl diethyl 4-phosphonocrotonamide (iv) N-2-Methylphenyl 4-bromocrotonamide (20 g) and triethylphosphite (16.7 g) heated together at 140° C. and the bromoethane produced removed by distillation.

Patent; Roussel Uclaf; US5270343; (1993); (A) English View in Reaxys 5 : EXAMPLE 5 EXAMPLE 5 A mixture of 4.40 g (10.1 mmol) of (RS)-2,2'-diiodo-6,6'-dimethylbiphenyl, 75 mg (0.42 mmol) of PdCl2 and 4.07 g (24.5 mmol) of triethyl phosphite was heated to 160° (bath temperature) while stirring.

The ethyl bromide formed was distilled off over a distillation bridge with the aid of a weak N2 stream.

Patent; Hoffmann-La Roche Inc.; US5302738; (1994); (A) English View in Reaxys The following compounds are preferred examples of the halocompounds of formula (III): Methyl bromide, Ethyl bromide, n-Propyl bromide, Bromoisopropane, Bromobutane, Bromohexane, Bromoheptane, Bromooctane, 1-Bromo-2-methylbutane, ...

Patent; Rhone-Poulenc Chimie; US5777151; (1998); (A) English View in Reaxys 2 : Stage C: Ethyl (E)-4-Diethoxyphosphoryl-3-Methyl-2-Butenoate Stage C: Ethyl (E)-4-Diethoxyphosphoryl-3-Methyl-2-Butenoate 50 mmol of ethyl (E)-4-bromo-3-methyl-2-butenoate are heated to 130°-140° C. with protection from moisture.

After the heating has been stopped, 50 mmol of triethyl phosphite are added dropwise so as to maintain the temperature at about 130° C.; the bromoethane formed becomes removed as soon as it appears.

When the addition is complete, the reaction is completed by heating for 30 minutes to 150°-160° C. A distillation under vacuum enables the expected product to be collected.

Yield: 94percent.

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

B.p.2: 150°-152° C. Alkyl (E)-4-diethoxyphosphoryl-3-methyl-2-butenoates are obtained in an identical manner using in stage A the alkyl (E)-3methyl-4-oxobutenoate corresponding to the expected product.

Patent; Adir et Compagnie; US4975454; (1990); (A) English View in Reaxys XXXVII.i : 1-[(Z)-1-Fluoro-3,3-dimethylbut-1-enyl]-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile i) A mixture of ethyl bromofluoroacetate (25 g) (Fluorochem.) and triethylphosphite (30 ml) was heated at 150°, in an apparatus set-up for fractional distillation, until production of bromoethane ceased.

Patent; The Wellcome Foundation Limited; US5116862; (1992); (A) English View in Reaxys 2 : EXAMPLE 2 EXAMPLE 2 The following two-flask synthesis resulted in a yield of 49.6 percent (not optimized) of a 52:48 exo:endo mixture of the isomers of brevicomin.

The reactions are illustrated in FIG. 3 wherein compounds similar to those of FIG. 1 have similar numerical designations.

To a solution of the acrolein dimer aldehyde (one equivalent) in anhydrous ether at 0° C. in a first flask, 1.3 equivalents of EtMgBr (3.1 molar in ether) was slowly added to form Compound 6.

The mixture was then stirred at 25° C. for one hour.

The reaction mixture was quenched with ice cold aqueous NH4 Cl solution and then equilibrated between ether and water.

The organic layer was washed with water and dried with anhydrous MgSO4.

Evaporation of the solvent gave the mixture of alcohols 2e, Li=H and 2t, Li=H) as a pale yellow oil.

The mixture of alcohols is generally indicated as Compound 7 and specifically shown as Compounds 2e and 2t in FIG. 2.

To the solution of the mixture of alcohols in anhydrous tetrahydrofuran (THF) at -78° C. contained in a second flask, 3 equivalents of t-BuLi (1.48 M in pentane) was added.

A canary yellow precipitate (t-BuLi-THF complex) was observed.

After the addition was complete, the bath was replaced by an ice bath.

The reaction mixture was stirred at 0° C. for one hour, diluted with anhydrous THF and recooled to -78° C. Freshly distilled methyl iodide was added and the bath was allowed to warm to 0° C. The reaction mixture was stirred at 0° C. for 4 hours and then quenched with water.

It was equilibrated between ether and water.

The organic layer was treated twice with 5percent HCl, once with water and then dried with anydrous MgSO4.

Evaporation of the solvent gave the mixture of brevicomins.

These were separated by flash chromatography (12percent EtOAc in hexanes).

The ethyllithium used in Example 1 can be obtained commercially or it can be prepared from bromoethane by the following procedure.

Patent; University of Pittsburgh; US4609743; (1986); (A) English View in Reaxys 10 : EXAMPLE 10 This 2-(4-methylphenyl)-4-methyl-pyrimidine is reacted with N-bromosuccinimide in the manner described in Example 3, yielding, after recrystallisation from ligroin, 2-(4-bromomethylphenyl)-4-methyl-pyrimidine with a melting point of 104°-106° C. A mixture consisting of 105 g of 2-(4-bromomethylphenyl)-4-methyl-pyrimidine and 265 g of triethyl phosphite is warmed slowly to 150° C., with stirring and whilst at the same time distilling off the ethyl bromide formed, and is then stirred for 5 hours at this temperature.

After distilling off the excess triethyl phosphite, 125 g of the phosphonate are obtained in the form of a pale brown, viscous oil.

Patent; Ciba-Geigy Corporation; US4297234; (1981); (A) English View in Reaxys 33.b : (b) (b) Formation of the carbanion of valeronitrile and alkylation with ethyl bromide The method described in paragraph (b) of Example 31 was employed except that the alkylation was performed between 28° and 30° C. and the reaction medium maintained for 1 hour at room-temperature before hydrolysis.

In this manner, 114 g of crude oil was obtained titrating 77.7percent in desired product.

Yield in 2-ethyl-valeronitrile: 80percent.

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Patent; Sanofi; US4377533; (1983); (A) English View in Reaxys Representative examples of the compound of general formula (III) are as follows: Methyl alcohol, methyl iodide, dimethyl sulfonate, methyl mercaptane, ethyl bromide, ethyl iodide, ethyl mercaptan, n-propyl chloride, n-propyl iodide, ...

Patent; Sanraku-Ocean Co., Ltd.; US4368203; (1983); (A) English View in Reaxys 16 : EXAMPLE 16 EXAMPLE 16 16.6 g of triethyl phosphite are added dropwise at 100° C. under nitrogen solution of 22.7 g (0.08 mol) of 5-ethoxy-2-(4'-bromomethylphenyl)-1,3,4-oxadiazole in 80 ml of toluene in such a manner that the bromoethane produced immediately distils off.

Patent; Bayer Aktiengesellschaft; US4510311; (1985); (A) English View in Reaxys 49 : EXAMPLE 49 EXAMPLE 49 20 g of triethylphosphite are added dropwise at 100° C. under nitrogen to a solution of 22.7 g (0.08 mol) of 5-ethoxy-3-(4-bromoethyl-phenyl)-1,2,4-oxadiazole in 80 ml absolute toluene, in such a manner that the bromoethane produced distils off immediately.

Patent; Bayer Aktiengesellschaft; US4510311; (1985); (A) English View in Reaxys I : Reaction of (n5 -C5 Me5)RhPMe3 (C2H5)(Br) with Br2 Reaction of (n5 -C5 Me5)RhPMe3 (C2H5)(Br) with Br2 A 10 ml flask equipped with a rubber septum and magnetic stirrer was changed with 20 mg of (n5 -C5 Me5) RhPMe3 (C2 H5) (Br), 8 ml of hexane and 5 μl of CHBr3 (as internal standard).

The stirred solution was cooled to -78° C. and a mixture Bromine/hexane (11 mg Br2 +1 ml hexane) was added over a period of 10 minutes.

The stirred solution was allowed to warm-up to room temperature and aliquot removed by syringe was analyzed by G C. From G. C. analysis, a calculated yield of bromoethane of approximately 80percent based on (n5 -C5 Me5)RhPMe3 (C2 H5)(Br).

Patent; The United States of America as represented by the United States Department of Energy; US4511745; (1985); (A) English View in Reaxys Representative compounds of formula (IV) include: methyl iodide, ethyl bromide, benzyl chloride, i-propyl chloride, n-propyl iodide, dimethyl sulphate, diethyl sulphate, di-n-propyl sulphate, phenylsulphonic acid methyl ester, and ...

Patent; Bayer Aktiengesellschaft; US3957779; (1976); (A) English View in Reaxys 3.A : EXAMPLE 3

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

A solution of 6.3 g. of 2-nitro-4-chlorobenzyl bromide and 4.2 g. of triethyl phosphite in 5 ml. of toluene was heated to 110° C. for 1 hour on an oil bath with stirring, and the ethyl bromide formed was removed therefrom.

Patent; Kitamura; Eiichi; Kitamura; Tetsuo; Kitamura; Tameo; US4013639; (1977); (A) English View in Reaxys METHOD ζ METHOD α Over about 30 minutes a solution of 27.2 parts of 4-(bromomethyl)-4'-cyanobiphenyl [formula 4] in 300 parts of dry xylene is added dropwise 20 parts of triethyl phosphite.

On completion of the addition the xylene and the ethyl bromide formed in the reaction are distilled off in a column.

Patent; Sandoz Ltd.; US4032558; (1977); (A) English View in Reaxys ...aving the formula (I): STR22 where: R1 and R2 each is alkyl or alkenyl having up to 4 carbon atoms or form together with the nitrogen atom to which they are bound pyrrolidino, piperidino or perhydroazepine; and RX is selected from the group consisting of hydrochloric acid, ... parachlorophenoxyacetic acid, parachlorophenoxyisobutyric acid, methyl bromide, methyl iodide, ethyl bromide, butyl bromide and benzyl bromide.

Patent; Innothera; US4079140; (1978); (A) English View in Reaxys Examples of the alkylating agent include a halogenated alkyl such as methyl chloride methyl bromide methyl iodide ethyl chloride ethyl bromide propyl chloride butyl bromide benzyl chloride benzyl bromide ...

Patent; Sumitomo Chemical Company, Limited; US4055565; (1977); (A) English View in Reaxys 28.ii : (ii) (ii) 1-Diphenylmethyleneindolizidine ethyl bromide Melting point: 163°-164° C. (colorless plate-like crystals) Patent; Hokuriku Pharmaceutical Co., Ltd.; US4205074; (1980); (A) English View in Reaxys Following compounds are considered as preferable among the said halogenated hydrocarbons: ethylbromide, methyliodide, n-propyliodide, n-butyliodide, 1-iodo-3-methylbutane, allylchloride, allylbromide, 3-chloro-1-butene, benzylchloride, benzylbromide, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodooctane, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-iododecane.

Patent; Tosoh Corporation; EP271212; (1988); (A2) English View in Reaxys 4 : EXAMPLE 4

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

A three neck 100 ml flask was arranged for product distillation and fitted with a stirrer and thermometer, then charged with 7.18 g of 2-(sulfophenyl) ethyl bromide, sodium salt, 16.6 g of triethylphosphite and 3.0 g of dimethylformamide.

This mixture was stirred and heated to 120°-130° C. and ethyl bromide slowly distilled out.

After maintaining the temperature for about two hours, the pasty mixture was cooled to room temperature and extracted twice with 75 ml portions of ethyl ether.

The solid product was a mixture of diethyl 2-(sulfophenyl) ethylphosphonate, sodium salt and 2-(sulfophenyl) ethyl bromide, sodium salt.

To a three necked 100 ml round bottom flask fitted with a reflux condenser, Dean-Stark trap, magnetic stirrer and nitrogen purge line was added a portion of the solid containing the above-prepared phosphonate and 20 ml of 48percent by weight hydrobromic acid.

The mixture was refluxed until the evolution of ethyl bromide into the trap ceased.

From the amount of ethyl bromide recovered, the initial weight of diethyl 2-(sulfophenyl) ethylphosphonate, sodium salt was calculated as 1.1 g.

Patent; Occidental Research Corporation; US4235991; (1980); (A) English View in Reaxys R.65 : 2-(4-Bipenylyl)ethylthiocyanate Reference Example 65 2-(4-Bipenylyl)ethylthiocyanate Bromine (1.5 ml) was added dropwise to an acetonitrile (60 ml) solution of triphenylphosphine (5 g).

After stirring for 5 minutes, an acetonitrile solution (30 ml) of 2-(4-biphenylyl)ethanol (5 g) was added to the reaction mixture.

The reaction mixture was stirred at room temperature for one hour and concentrated.

Diethyl ether was added to the residue.

The supernatant was collected, then dried and concentrated.

The residue was purified by silica gel column chromatography (eluent: IPE) to obtain 2-(4-bipenylyl)ethylbromide(6 g).

Patent; Takeda Chemical Industries, Ltd.; US6329389; (2001); (B1) English View in Reaxys Preferred compounds of the formula (II) are: methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl bromide, ethyl iodide, benzyl chloride, benzyl bromide and benzyl iodide.

Patent; Wischnat, Ralf; Rudolph, Joachim; US2004/19219; (2004); (A1) English View in Reaxys 3 : Benzyl 3-diethylphosphonopropionate 56.8 mmol of benzyl 3-bromopropionate (13.8 g) and 1.7 eq of triethyl phosphite (16.0 g) are heated to 140° C. with stirring in a distillation apparatus sealed with a gas balloon for pressure equalization.

The bromoethane formed during the reaction is distilled out continuously and collected in a receiver flask cooled to 0° C. After 4 h, the remaining oily residue is fractionally distilled under high vacuum through a Vigreux column; the product is a colourless oil.

Yield: 12.1 g (40.3 mmol, 71percent), slightly impure, Rf=0.33 (A:H 2:3) For greater purity, the product can be purified where appropriate by flash chromatography (eluent A:H 2:3).

Patent; Meyer, J?ouml;rg; Nies, Berthold; Dard, Michel; Holzemann, Gunter; Kessler, Horst; Kantlehner, Martin; Hersel, Ulrich; Gibson, Christoph; Sulyok, Gabor; US2004/29782; (2004); (A1) English View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br O

Br

O P Br

O

O

P

O

O O

O

Br

Rx-ID: 23135950 View in Reaxys 28/328 Yield

Conditions & References 1.3 : 1-3) 4-(2-Bromo-5-methoxybenzyl)piperidine hydrochloride 1-3) 4-(2-Bromo-5-methoxybenzyl)piperidine hydrochloride A mixture of 2-bromo-5-methoxybenzyl bromide (33.2 g) and triethyl phosphite (19.2 g, 116 mmol) was stirred at 90°C for 12 hours..

The bromoethane produced was distilled off to obtain 42.4 g of a crude product of diethyl 2-bromo-5-methoxybenzylphosphonate. NMR (CDCl3) α 1.27 (t, 6H, J = 6.9 Hz), 3.37 (d, 2H, J = 22.1 Hz), 3.79 (s, 3H), 3.98-4.16 (m, 4H), 6.63-6.72 (m, 1H), 7.02 (t, 1H, J = 2.8 Hz), 7.43 (d, 1H, J = 8.6 Hz). , Time= 12h, T= 90 °C Patent; Sumitomo Pharmaceuticals Company, Limited; EP1466901; (2004); (A1) English View in Reaxys O

O

O P O

O

Br

O

O

Br

P

O O

O

Rx-ID: 23135962 View in Reaxys 29/328 Yield 76 %

Conditions & References A.A24 : EXAMPLE A24 [0513] Diethyl [4-(ethoxycarbonyl)phenyl]-methanephosphonate 55 ml (0.316 mol) triethyl phosphite were placed in a stirring apparatus and pre-heated to an internal temperature of 90° C. The suspension of 60.0 g (0.247 mol) ethyl 4-(bromomethyl)-benzoate in 100 ml dichloromethane was slowly added thereto in small batches, while the ethyl bromide formed and the evaporating dichloromethane were continuously distilled off. Once the quantity of ethyl bromide formed had significantly diminished, the reaction temperature was slowly increased to 140° C. and this temperature was maintained until the formation of ethyl bromide had ended (approx. 2 hours). The excess triethyl phosphite was eliminated in vacuo, the residue was suspended in a little ethyl acetate and purified by column chromatography on silica gel using ethyl acetate/petroleum ether (gradient 1/1-->1/0 v/v) as eluant. After working up in the usual way 56.3 g (76percent of theory) of the above title compound were obtained in the form of a colourless oil. in dichloromethane, Time= 2h, T= 90 - 140 °C Patent; Boehringer Ingelheim International GmbH; US2004/192729; (2004); (A1) English View in Reaxys O

O P

O

Br Br

Br

O

O P

Br

O

Rx-ID: 23222795 View in Reaxys 30/328 Yield 73 %

Conditions & References 4 : EXAMPLE 4; Preparation of 3-Bromopropylphosphonic Acid Diethylester

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

471 g (238 ml, 2.33 mol) 1,3-dibromopropane and 77.6 g (81 ml, 0.467 mol) triethylphosphite were introduced into a 500 ml flask and heated for 30 minutes to 155-160° C. 20 ml ethyl bromide (boiling point: 40° C.) were distilled off under normal pressure via a reflux condenser and a distilling apparatus.

Concentration of the solution under vacuum (8 torr (1.07*103Pa)) resulted in 380 g (191 ml, 1.863 mol) 1.3 dibromopropane (surplus educt).

88.1 g (0.34 mol) could be distilled as a colourless liquid (boiling point: 96° C., 0.1 torr (13.33 Pa)) from the remaining yellow oil.

This corresponds to a yield of 73percent. (Hewitt, Teese, Aust.J.Chem. 1984, 37, 205-10 U.S. Pat. No. 4,206,156).

1H-NMR (CDCl ) α=4.08 (quintet, J=7 Hz, 4H), 1.33 (t, J=7 Hz, 6H); 13C-NMR (CDCl ) α=61.2 (OCH CH ), 33.10 (J=18, 3 Hz), 3 3 2 3 25.6 (J=4, 4 Hz), 24.14 (J=120, 6 Hz) 16.04 (OCH2CH3). , Time= 0.5h, T= 155 - 160 °C Patent; Hassan, Jomaa; US6680308; (2004); (B1) English View in Reaxys

Br

O O

PH

(v5)

O

Rx-ID: 23936632 View in Reaxys 31/328 Yield

Conditions & References

11.3 g (80%)

5 : Synthesis of Compound (2A) The 5-hydroxy-5H-dibenz[a,d]cycloheptene (9.0 g, 43.2 mmol) was mixed with 50 ml of acetyl bromide, followed by heating under reflux for about 30 minutes.

The excess acetyl bromide was removed by evaporation under reduced pressure, and 70 g (421 mmol) of triethyl phosphite was added to the residue.

The mixture was slowly heated up to 150° C. (external temperature), at which the mixture was kept for about 2.5 hours while driving the by-produced bromoethane out of the system.

The excess triethyl phosphite was removed by evaporation under reduced pressure, water added to the residue, and the mixture extracted with ethyl acetate.

The extract was purified by silica gel column chromatography to yield 11.3 g (80percent) of 5H-dibenz[a,d]cycloheptenyl phosphonate.

Patent; FUJI PHOTO FILM CO., LTD.; US2003/65171; (2003); (A1) English View in Reaxys I

Br

Rx-ID: 632106 View in Reaxys 32/328 Yield

Conditions & References With bromide in methanol, acetonitrile, T= 30 °C , ΔH(excit.); -ΔS(excit.); different solvent mixtures, Rate constant, Thermodynamic data Kondo, Yasuhiko; Kusabayashi, Shigekazu; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol. 78; (1982); p. 109 - 118 View in Reaxys With bromide in methanol, T= 30 °C , further solvent mixture, ΔH(excit.), Rate constant, Thermodynamic data Yasuhiko, Kondo; Kazumi, Yuki; Takeshi, Yoshida; Niichiro, Tokura; Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases; vol. 76; (1980); p. 812 - 824 View in Reaxys

38 % Spectr.

With tributyltin bromide in pyridine, T= 100 °C , Δ G, Thermodynamic data, Equilibrium constant

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Friedrich, Edwin C.; Abma, Charles B.; Journal of the American Chemical Society; vol. 102; nb. 4; (1980); p. 1367 - 1371 View in Reaxys With lithium bromide in acetone, T= 24.8 °C , ΔH(excit.), ΔS(excit.); var. temp., Equilibrium constant, Rate constant, Thermodynamic data Satoh, Masahiro; Hirota, Minoru; Bulletin of the Chemical Society of Japan; vol. 69; nb. 9; (1996); p. 2619 - 2624 View in Reaxys With bromide in acetonitrile, T= 25 °C , reaction enthalpy, Thermodynamic data Kondo, Yasuhiko; Tsukamoto, Tamio; Kimura, Naoko; Journal of the Chemical Society. Perkin Transactions 2; nb. 9; (1997); p. 1765 - 1769 View in Reaxys With bromine Friedel; Justus Liebigs Annalen der Chemie; vol. 135; (1865); p. 206 View in Reaxys With tetramethylammonium bromide in acetonitrile, T= 30 °C , Thermodynamic data, Further Variations: Solvents Kondo, Yasuhiko; Urade, Miyuki; Yamanishi, Yukari; Chen, Xinyu; Journal of the Chemical Society, Perkin Transactions 2; nb. 8; (2002); p. 1449 - 1454 View in Reaxys With tetramethylammonium bromide in acetonitrile, T= 30 °C Kondo, Yasuhiko; Urade, Miyuki; Yamanishi, Yukari; Chen, Xinyu; Journal of the Chemical Society, Perkin Transactions 2; nb. 8; (2002); p. 1449 - 1454 View in Reaxys

Br

O

N

O OH

Rx-ID: 25414516 View in Reaxys 33/328 Yield

Conditions & References 16.4 : Example 16.4 Example 16.4 In analogy to examples 16.2 and 16.3, from trans-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-carbamic acid benzyl ester and bromoethane, trans-Ethyl-(4-hydroxy-cyclohexyl)-carbamic acid benzyl ester was obtained as orange oil, MS: 277 (M).

Patent; Ackermann, Jean; Aebi, Johannes; Blum, Denise; Chucholowski, Alexander; Dehmlow, Henrietta; Maerki, Hans-Peter; Morand, Olivier; Trussardi, Rene; von der Mark, Elisabeth; Wallbaum, Sabine; Weller, Thomas; US2002/45777; (2002); (A1) English View in Reaxys O

O P O

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

O

Br

P

B

O

Br

O

Br

O

O P+

Br B– Br

O P+

Br B–

O

O

Br

Br

Br

B

Br

Br

Rx-ID: 8735433 View in Reaxys 34/328 Yield

Conditions & References With boron tribromide in chloroform-d1, Product distribution Lewkowski, Jaroslaw; Mortier, Jacques; Vaultier, Michel; Monatshefte fur Chemie; vol. 131; nb. 7; (2000); p. 707 - 710 View in Reaxys O

O

Br

Br

N

CH 2

O

(v2)

N

O

Rx-ID: 4925532 View in Reaxys 35/328 Yield

Conditions & References With ruthenium(II), tert-butyl alcohol in water, T= 22 - 23 °C , Irradiation, Rate constant Merenyi, Gabor; Lind, Johan; Eberson, Lennart; Acta Chemica Scandinavica; vol. 52; nb. 1; (1998); p. 62 - 66 View in Reaxys O

O

Br

P Br

Br

O

O

Br

P O

O

Rx-ID: 5106999 View in Reaxys 36/328 Yield

Conditions & References Time= 4.5h, T= 132 °C , other temp.; activation energy, Kinetics, Rate constant, Thermodynamic data Azzouz, Abdelkrim; Didi, Mohamed-Amine; Revue Roumaine de Chimie; vol. 43; nb. 4; (1998); p. 309 - 313 View in Reaxys Time= 4.5h, T= 132 °C Azzouz, Abdelkrim; Didi, Mohamed-Amine; Revue Roumaine de Chimie; vol. 43; nb. 4; (1998); p. 309 - 313 View in Reaxys

O

O

O

P Br

Br Br

O

O

O

P O

O P

O

Rx-ID: 5107000 View in Reaxys 37/328 Yield

Conditions & References T= 150 °C , other temp.; activation energy, Kinetics, Rate constant, Thermodynamic data Azzouz, Abdelkrim; Didi, Mohamed-Amine; Revue Roumaine de Chimie; vol. 43; nb. 4; (1998); p. 309 - 313 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

Br

O–

S+ O

Cl OO

S

S

S

S

S

O

Rx-ID: 5127361 View in Reaxys 38/328 Yield

Conditions & References With 18-crown-6 ether, potassium bromide in acetonitrile, T= 23 °C , Rate constant Zhao, Wenyi; Shine, Henry J.; Canadian Journal of Chemistry; vol. 76; nb. 6; (1998); p. 695 - 702 View in Reaxys With tetrabutylammomium bromide in acetonitrile, T= 23 °C , Rate constant Zhao, Wenyi; Shine, Henry J.; Canadian Journal of Chemistry; vol. 76; nb. 6; (1998); p. 695 - 702 View in Reaxys

O

Br

O

O

P

O

Br

O

P O

O

P

O

O

O P

O

O

Rx-ID: 5132384 View in Reaxys 39/328 Yield

Conditions & References T= 150 °C Azzouz, Abdelkrim; Didi, Mohamed-Amine; Revue Roumaine de Chimie; vol. 43; nb. 4; (1998); p. 309 - 313 View in Reaxys Br Br

O

O

Rx-ID: 24597358 View in Reaxys 40/328 Yield

Conditions & References 2.b : b) b) Preparation of Ethyl 0,0-diethyl-4-phosphono-2-methyl-2-butenoate 2899 g (17.1 mol) of 98percent strength triethyl phosphite were placed in the reactor and heated to 90° C. Over a period of 2 h, 3317 g of crude ethyl bromobutenoate prepared as described under 2a) were added dropwise.

The reaction began immediately on commencement of metering.

Ethyl bromide (bp 38° C.) formed during the reaction was continuously distilled off through a Vigreux column.

On completion of the addition stirring was continued for 1 h at 90° C. The crude ethyl 0,0-diethyl-4-phosphono-tiglic acid ester was freed from low-boiling components (bp ca 55° C.) at 120° C. down to a reduced pressure of 15 mbar.

Following removal, by distillation, of the low-boiling components the temperature was raised to 140° C. and the pressure reduced to 5 mbar at and a moderately volatile fraction was removed by distillation (bp ca 75° C.).

The residues of ethyl 0,0-diethyl-4-phosphono-2-methyl-2-butenoate (yellowish orange oil) remaining after cooling to 25° C. can be further processed in this quality in Horner-Emmons reactions.

Patent; BASF Aktiengesellschaft; US5717128; (1998); (A) English View in Reaxys

Br

O Br O

Rx-ID: 24597359 View in Reaxys 41/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References 1.b : b) b) Conversion of the Crude Bromo-2-methyl-butenoate Mixture to Ethyl 0,0-diethyl-4-phosphono-tiglic Acid Ester 2899 g (17.1 mol) of 98percent strength triethyl phosphite were placed in the reactor and heated to 120° C. 3250 g of crude ethyl bromo-2-methyl-butenoate mixture prepared as described under 1a were added dropwise over a period of 2 h.

The reaction began immediately metering commenced.

Ethyl bromide (bp 38° C.) formed during the reaction was continuously distilled off through a Vigreux column.

On completion of the addition stirring was continued for 30 min at 120° C. The crude ethyl 0,0-diethyl-4-phosphono-2-methyl-2-butenoate was freed from low-boiling components at 120° C. down to a reduced pressure of 15 mbar (bp of the low-boiling fractions 50°-60° C.).

Following removal, by distillation, of the low-boiling components the pressure was decreased, at an internal temperature of 120° C., to 5 mbar and a moderately volatile fraction was distilled off at 80° C. The residues of ethyl 0,0-diethyl-4-phosphono-2-methyl-2-butenoate remaining on cooling to 25° C. (yellowish orange oil) were used in this quality as a building block for Horner-Emmons reactions for the preparation of α-apo-carotenic acid esters.

Patent; BASF Aktiengesellschaft; US5717128; (1998); (A) English View in Reaxys Br –H

2C

Br

Cl

Rx-ID: 4561620 View in Reaxys 42/328 Yield

Conditions & References T= 24.9 °C , Rate constant Born, Monique; Ingemann, Steen; Nibbering, Nico M. M.; Journal of the Chemical Society. Perkin Transactions 2; vol. 0; nb.

11; (1996); p. 2537 - 2547; Art.No: 6/00223D View in Reaxys Br

Br Br

Br Br

Br

Br

Rx-ID: 4562539 View in Reaxys 43/328 Yield 53 % Turnov., 3 % Turnov., 17 % Turnov.

Conditions & References With 2AlBr3*CBr4, bromine, Time= 3h, T= 55 - 65 °C , p= 760Torr , Title compound not separated from byproducts Akhrem; Orlinkov; Afanas'eva; Vol'pin; Russian Chemical Bulletin; vol. 45; nb. 5; (1996); p. 1148 - 1153 View in Reaxys

Br

Br Br

Rx-ID: 4562540 View in Reaxys 44/328 Yield

Conditions & References

5 % Turnov., 104 % Turnov.

With 2AlBr3*CBr4, bromine, Time= 18h, T= 55 - 65 °C , p= 34200Torr , Title compound not separated from byproducts

5 % Turnov., 104 % Turnov.

With 2AlBr3*CBr4, bromine, Time= 18h, T= 55 - 65 °C , p= 34200Torr , other alkanes, other reagents and reaction conditions,

Akhrem; Orlinkov; Afanas'eva; Vol'pin; Russian Chemical Bulletin; vol. 45; nb. 5; (1996); p. 1148 - 1153 View in Reaxys

Product distribution Akhrem; Orlinkov; Afanas'eva; Vol'pin; Russian Chemical Bulletin; vol. 45; nb. 5; (1996); p. 1148 - 1153 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

F

O F

OH O

OH

Br

N

O O

N

HO

O F

HO

O

F

Rx-ID: 24520509 View in Reaxys 45/328 Yield 88%

Conditions & References 1,2-bis(2-amino-5,6-difluorophenoxy)ethane-N,N,N',N'-tetraacetic acid (5) 1,2-bis(2-amino-5,6-difluorophenoxy)ethane-N,N,N',N'-tetraacetic acid (5) A mixture of 115 mg of tetrabenzyl ester 4, 2 mL of 0.6M NaOH, and 5 mL of methanol was allowed to stand at room temperature for 48 hours.

The organic solvent was removed, 10 mL of water added and the solution extracted with ether.

The aqueous solution was acidified with 6N HCl and the precipitated product collected and dried to yield 45 mg of white crystals, m.p. 236°-239° C. Compounds Described on Page 25: 1-bromo-2-(4-benzyloxy-2-nitrophenoxy)ethane (6) A mixture of 4-benzyl-2-nitrophenol (1.3 g, 5.3 mmol) and K2 CO3 (1.2 g, 8.7 mmol) in DMF (10 mL) was stirred for 10 min.

Dibromoethane (1.4 mL, 16.2 mmol) was added to the reaction mixture and heated at 70° C. for 24 hrs.

The reaction mixture was diluted with ether (30 mL) and washed with water (20 mL) and brine (20 mL).

The ether layer was dried (MgSO4) and concentrated under reduced pressure.

The crude product was fractionated by flash chromatography (4:1 hexane/ethyl acetate) yielding bromoethane 6 as a yellow oil (1.3 g, 88percent).

1 H NMR: 3.65 (t, J=5 Hz, 2H), 4.35 (t, J=5 Hz, 2H), 5.05 (s, 2H), 7.0-7.5 (m, 8H).

Patent; The United States of America as represented by the Department of Health and Human Services; US5516911; (1996); (A) English View in Reaxys

Br

O

O

O P

O

O

Rx-ID: 24461572 View in Reaxys 46/328 Yield

Conditions & References 1 : EXAMPLE 1 For example, 153 grams of bromoacetaldehyde diethyl acetal was placed in a three-neck flask equipped with a magnetic stirrer.

A gentle stream of nitrogen purged the system.

To the stirred solution, 22.1 grams of triethylphosphite was added drop-wise over a period of approximately 25 minutes.

During this time, the temperature of the solution rose from approximately 110° C. to approximately 120° C. After the addition of the triethylphosphite was complete, the mixture was stirred for about 4 hours at the temperature of about 160° C. The ethyl bromide which evolved during the reaction was recovered through a condenser.

The low boiling point fractions were removed with a water pump while the residual oil was fractionated under reduced pressure at temperature of approximately 72°-79° C. The percent yield of compound 1 was about 67percent.

Patent; Research Foundation of the State of New York; US5449736; (1995); (A) English View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O P

Br O

O N

Rx-ID: 24520508 View in Reaxys 47/328 Yield

Conditions & References A : Diethyl 4-cyanobenzylphosphonate EXAMPLE A Diethyl 4-cyanobenzylphosphonate 98 g of 4-(bromomethyl)benzonitrile and 300 ml of triethyl phosphite are heated at 140° C. until the reaction is initiated.

The mixture is then reflux-heated at a bath temperature of 150°-160° C. for a further 2 hours, the ethyl bromide formed is removed by distillation, the mixture is heated at 150° C. for a further hour and triethyl phosphite is then removed by distillation in vacuo.

The residue is treated with 250 ml of cyclohexane in an ice bath, and the crystals formed are suction-filtered and washed with 150 ml of cyclohexane. 125.6 g (99.2percent of theory) of the title compound of melting point 41.5°-43° C. are obtained.

Patent; Dr. Karl Thomae GmbH; US5466687; (1995); (A) English View in Reaxys

HN

Br

Cl

H

N O

Rx-ID: 24367073 View in Reaxys 48/328 Yield

Conditions & References 4.7.9 : 5-(N-Acetyl-N-ethyl-amino)-2-n-propylamino-tetralinehydrochloride Example 4.7.9 5-(N-Acetyl-N-ethyl-amino)-2-n-propylamino-tetralinehydrochloride Starting from 2.35 g (0.0095 mol) of 5-acetylamino-2-n-propylamino-tetraline (Example 4.1.1) and 1.07 g (0.0098 mol) of ethylbromide the base of the title compound is obtained analogously to Example 4.7.1 and crystallized as the hydrochloride.

Yield 1.60 g (54.2percent of theory), melting point 257° C. Patent; Boehringer Ingelheim KG; US5196454; (1993); (A) English View in Reaxys

O

O

O P

Br

O

O

O

Rx-ID: 24367074 View in Reaxys 49/328 Yield

Conditions & References 1.A : STEP A: STEP A: Methyl 5-(diethoxy phosphoryl)-4-oxo-pentanoate 10.5 ml of triethyl phosphite were added to 12.54 g of methyl 5-bromo-4-oxo-pentanoate and the mixture was heated at 140° C with stirring.

After reflux for one hour, the ethyl bromide formed was distilled off.

After rectification under reduced pressure, 13.5 g of a colorless oil were obtained with a boiling point of 155° C at 0.1 mm Hg. Patent; Roussel Uclaf; US5210093; (1993); (A) English View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

N

Br

OH

P

S

N Br

P

S O

Rx-ID: 1526631 View in Reaxys 50/328 Yield

Conditions & References With ethanethiol, Time= 2h, Heating, Product distribution, Mechanism Allen, David W.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 66; nb. 1.4; (1992); p. 73 - 78 View in Reaxys Br

2''-N-t-Butoxycarbonyl-6-0-ethyl-3',4'-0-isopropylideneelsamicin A Rx-ID: 25414518 View in Reaxys 51/328

Yield

Conditions & References

94%

9 : Synthesis of 2''-N-t-Butoxycarbonyl-6-0-ethyl-3',4'-0-isopropylideneelsamicin A (6b) EXAMPLE 9 Synthesis of 2''-N-t-Butoxycarbonyl-6-0-ethyl-3',4'-0-isopropylideneelsamicin A (6b) Alkylation reagent: Ethyl bromide (the reaction was carried out in the presence of KI) Yield: 94percent MP 161-183°C. IR αmax(KBr) cmmin 1 3420, 2970, 2925, 2860, 1735. UV αmax(MeOH) nm (α) 236 (35800), 266 (40100), 326 (7360), 369 (8960), 390 (12700), 411 (13200).

NMR (CDCl3) α 0.65 (9H, s), 1.15-1.85 (18H), 2.90 (3H, s), 4.25 (2H, q, J=7 Hz), 5.25 (1H, d, J=8 Hz), 5.80 (1H, d, J=4 Hz),

1H

8.23 (1H, dd, J=8 and 1 Hz).

Patent; Bristol-Myers Squibb Company; EP516157; (1992); (A1) English View in Reaxys F

F

F

O

H

F

O Br

P

F

O

Br F

F

O

O F

F

F

Rx-ID: 3379987 View in Reaxys 52/328 Yield 55 %

Conditions & References Time= 1.66667h, T= 140 - 150 °C , Title compound not separated from byproducts Maslennikov, I. G.; Matus, L. I.; Kirichenko, L. N.; Lavrent'ev, A. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 61; nb. 2; (1991); p. 513,467 View in Reaxys Br

ethyl (E/Z-4-diethylphosphono)-3-methylbut-2-enoate Rx-ID: 25414517 View in Reaxys 53/328 Yield

Conditions & References l.4.a : Example l5 (a)

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

A mixture of ethyl 3-methylbut-2-enoate (l0.lg), N-bromosuccinimide (l4g) and benzoyl peroxide (0.lg) in dry carbon tetrachloride (l50 ml) was stirred under reflux for 3h, filtered, solvent evaporated under reduced pressure and residue distilled to yield ethyl (E/Z-4-bromo-3-methylbut-2-enoate (9.4g, b.pt. l00-l05° l5mmHg. nD=l.4863.) which was then added dropwise to triethyl phosphite (3.lg) at l00°.

The temperature was slowly raised to l50°C and the ethyl bromide formed allowed to distil over.

After 2h, the residue was distilled to give ethyl (E/Z-4-diethylphosphono)-3-methylbut-2-enoate (2.lg, b.pt. l06-l20°C at 0.2mmHg. nD= l.4555.).

An earlier fraction (l.2g) from the distillation also contained mainly the required products.

Patent; THE WELLCOME FOUNDATION LIMITED; EP251472; (1991); (B1) English View in Reaxys

O

Br

O

O

P

Br

O

O

O

P O O

Rx-ID: 1862825 View in Reaxys 54/328 Yield

Conditions & References With nickel dichloride, T= 160 - 170 °C Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 1.1.; (1990); p. 58 61,50 - 52 View in Reaxys

O

Br

O

O

P

Br

O

O P

O

Rx-ID: 1922164 View in Reaxys 55/328 Yield

Conditions & References With nickel dichloride, T= 175 - 180 °C Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 1.1.; (1990); p. 58 61,50 - 52 View in Reaxys

O

Br O

Br P

O

O

O

P O

O O

Rx-ID: 1984481 View in Reaxys 56/328 Yield

Conditions & References With nickel dichloride Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 1.1.; (1990); p. 58 61,50 - 52 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O O

Br P

O Br

P

O O

O

Rx-ID: 1984507 View in Reaxys 57/328 Yield

Conditions & References With nickel dichloride, T= 170 - 175 °C Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 1.1.; (1990); p. 58 61,50 - 52 View in Reaxys Br CH 2

Rx-ID: 2247612 View in Reaxys 58/328 Yield

Conditions & References With bromine, T= 24.9 °C , other temperatures, Kinetics Timonen, R. S.; Seetula, J. A.; Gutman, D.; Journal of Physical Chemistry; vol. 94; nb. 7; (1990); p. 3005 - 3008 View in Reaxys

O

O P

O

Br Br

O

O

P O

Rx-ID: 3874441 View in Reaxys 59/328 Yield

Conditions & References With tetrakis(triethylphosphite)nickel(0), other arylhalides, various P(III) ester, other Ni(0) complexes, Mechanism Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 5; (1990); p. 1040 1042,917 - 919 View in Reaxys

Br

O

O P Br

O

O

O

P

O

O O

Rx-ID: 3874684 View in Reaxys 60/328 Yield 78.0 %

Conditions & References With nickel dichloride, Time= 0.0833333h, T= 180 - 185 °C , reaction with other aryl halides: influence of the nature of the aryl halides used on the ease of Arbuzov reaction Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 12.1; (1989); p. 2406 2407 View in Reaxys

78 %

With nickel dichloride, Time= 0.0833333h, T= 180 - 185 °C , Heating Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 12.1; (1989); p. 2406 2407

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys With nickel dichloride, T= 180 - 185 °C Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 1.1.; (1990); p. 58 61,50 - 52 View in Reaxys

Br

O

P

O

Si

P

Si

O

O

O

O

Br

O

O

Rx-ID: 3877129 View in Reaxys 61/328 Yield

Conditions & References With nickel dichloride, T= 160 - 170 °C , other P(III)-compounds Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 1.1.; (1990); p. 58 61,50 - 52 View in Reaxys With nickel dichloride, T= 160 - 170 °C Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 1.1.; (1990); p. 58 61,50 - 52 View in Reaxys

O

Br

O

O

Br

P

O

O

P

O

O

O

Rx-ID: 3924126 View in Reaxys 62/328 Yield

Conditions & References With nickel dichloride Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 60; nb. 1.1.; (1990); p. 58 61,50 - 52 View in Reaxys

(v4)

(v5) (v4)Co 2+

H 3N

(v4)

(v6) Br H 3N Co 2+NH 3 H 3N (v4) NH 3

(v4)

N

N H

Br

N H

(v4)N (v4) (v4)

(v4)

Rx-ID: 26713372 View in Reaxys 63/328 Yield

Conditions & References Kinetics, at 25°C Lee, Shaoyung; Espenson, James H.; Bakac, Andreja; Inorganic Chemistry; vol. 29; (1990); p. 3442 - 3447 ; (from Gmelin) View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O O

Br

O

Br

P

N

O

Cl P O

Br

Cl

N

O

Br

Rx-ID: 1615949 View in Reaxys 64/328 Yield

Conditions & References

65 %, 40 %

With iron(III) chloride, Time= 0.5h, T= 95 - 115 °C Silina, E. B.; Kozhushko, B. N.; Shokol, V. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 31; (1989); p. 571 - 586,505 517 View in Reaxys

Cl

Br

O

Br

Br Br

P Cl

O

N

Br

Cl P

Br Cl

N

O

O

Rx-ID: 1852774 View in Reaxys 65/328 Yield

Conditions & References

65 %, 58 %

With iron(III) chloride, T= 115 °C Silina, E. B.; Kozhushko, B. N.; Shokol, V. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 31; (1989); p. 571 - 586,505 517 View in Reaxys O

Cl

Br

O

Br

P

O

Cl P

N

Cl

Br

Cl

O

N Br

Rx-ID: 1852775 View in Reaxys 66/328 Yield

Conditions & References

65 %, 54 %

With iron(III) chloride, Time= 0.5h, T= 95 - 115 °C Silina, E. B.; Kozhushko, B. N.; Shokol, V. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 31; (1989); p. 571 - 586,505 517 View in Reaxys O

O

Br

O

Br

P

O

O

Br

F

F P

N

N

O

Br

Rx-ID: 1856113 View in Reaxys 67/328 Yield

Conditions & References

65 %, 60 %

With iron(III) chloride, Time= 0.5h, T= 95 - 115 °C Silina, E. B.; Kozhushko, B. N.; Shokol, V. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 31; (1989); p. 571 - 586,505 517 View in Reaxys O

F

Br

O

Br

P

O

N

F

Br

F

O

F P

N

Br

Rx-ID: 1976506 View in Reaxys 68/328 Yield 65 %, 72 %

Conditions & References With iron(III) chloride, Time= 0.5h, T= 95 - 115 °C

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Silina, E. B.; Kozhushko, B. N.; Shokol, V. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 31; (1989); p. 571 - 586,505 517 View in Reaxys

O

O P

O Br

Br

O

O

P

O

O

O

Rx-ID: 2410813 View in Reaxys 69/328 Yield

Conditions & References

65 %

With nickel dichloride, Time= 0.0833333h, T= 165 - 175 °C Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 12.1; (1989); p. 2406 2407 View in Reaxys

O

Br

O P

O

Br

O

O

P O O

O

Rx-ID: 2948660 View in Reaxys 70/328 Yield

Conditions & References

60 %

With nickel dichloride, Time= 0.0833333h, T= 165 - 175 °C Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 12.1; (1989); p. 2406 2407 View in Reaxys

O

O P

O Br

O

Br

O

O

P

O

O

Rx-ID: 3874443 View in Reaxys 71/328 Yield

Conditions & References

80 %

With nickel dichloride, Time= 0.0833333h, T= 170 - 175 °C , Heating Sentemov, V. V.; Krasil'nikova, E. A.; Berdnik, I. V.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 12.1; (1989); p. 2406 2407 View in Reaxys Br

Br

Br

Br O

Rx-ID: 3954165 View in Reaxys 72/328 Yield

Conditions & References With bromine, p= 3Torr , Irradiation, infrared multiple-photon decomposition, Product distribution, Mechanism Majima, Tetsuro; Ishii, Tadahiro; Arai, Shigeyoshi; Bulletin of the Chemical Society of Japan; vol. 62; nb. 6; (1989); p. 1701 - 1709 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

F

F

F

F

Br

Br

C

C

F

F

Rx-ID: 3954247 View in Reaxys 73/328 Yield

Conditions & References With bromine in gas, T= 22 - 25 °C , p= 0.4 - 11.3Torr , Rate constant, Mechanism Edelbuettel-Einhaus; Hoyermann; Rohde; Wagner; Hack; Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics; vol. 93; nb. 12; (1989); p. 1413 - 1416 View in Reaxys

Br

Br

Br

Br

O

Br

Rx-ID: 3956312 View in Reaxys 74/328 Yield

Conditions & References With bromine, p= 3Torr , Irradiation, infrared multiple-photon decomposition, Product distribution, Mechanism Majima, Tetsuro; Ishii, Tadahiro; Arai, Shigeyoshi; Bulletin of the Chemical Society of Japan; vol. 62; nb. 6; (1989); p. 1701 - 1709 View in Reaxys Br I

Rx-ID: 25413213 View in Reaxys 75/328 Yield

Conditions & References 1 : (1R,2S,4R)-2-(Substituted-methyloxy)-4-alkoxy-6,8-dioxabicyclo[3.2.1]octanes from Levoglucosenone methyl iodide or ethyl bromide) the following compounds were prepared: 1 (1R,2S,4R)-2-cyclobutanemethyloxy-4-methoxy-6,8-dioxabicyclo[3.2.1]octane, [α]D- 59.0°; 1 3C-nmr data: 100.1 (C-5), 74.7 and 74.5 (C-1 and C-4), 73.5 (RCH2O), 73.3 (C-2), 65.3 (C-7), 56.9 (OCH3), 34.8 (CH in cyclo-C4H7), 24.9, 24.8 and 18.3 (CH2 in cyclo-C4H7) and 23.8 (C-3).

Patent; HER MAJESTY THE QUEEN IN RIGHT OF NEW ZEALAND,DEPARTMENT OF SCIENTIFIC AND INDUSTRIAL RESEARCH,CHEMISTRY DIVISON; EP302599; (1989); (A2) English View in Reaxys

N

(v4)

O–

N

(v4) + (v4) N Co (v6) (v4)

O

Br

Cl OO

N

Rx-ID: 26367455 View in Reaxys 76/328 Yield

Conditions & References

97 %, <1, 3.8 %

With bromine in acetonitrile, one-electron oxidn. of cis-Co complex by Br2 at 298 K; monitored by (1)H-NMR Ishikawa, Kunio; Fukuzumi, Shunichi; Tanaka, Toshio; Inorganic Chemistry; vol. 28; (1989); p. 1661 - 1665 ; (from Gmelin) View in Reaxys Br

Br

Br

Sb

Br

H2 C

Sb

Br

Br

Rx-ID: 26552606 View in Reaxys 77/328 Yield 90.3 %

Conditions & References in diethyl ether, react. under dry Ar, stirring at room temp. (0.5 h); distilling, elem. anal.

Ates, Mustafa; Breunig, Hans Joachim; Guelec, Sabahittin; Journal of Organometallic Chemistry; vol. 364; (1989); p. 67 72 ; (from Gmelin)

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys

(v5)H

(v5)

H H

(v5)

H

H

(v5)

F F

B– FF

Re

N

O

(v2)

Br–

+P

(v8)

N+

P

P

I

-1 F (v4)

F (v5)

Br

(v5)

(v5)

B FF

(v5)

Re P N (v8)(v4) I O (v4)

P

(v3)

N+

P

Rx-ID: 26598110 View in Reaxys 78/328 Yield

Conditions & References

84 %, 96 %

in dichloromethane-d2, (N2); react. of Re complex and Ph3PNPPh3(1+) in CD2Cl2 at room temp.; not isolated, detected by (13)C- and (31)P-NMR Winter, Charles H.; Veal, William R.; Garner, Charles M.; Arif, Atta M.; Gladysz, J. A.; Journal of the American Chemical Society; vol. 111; nb. 13; (1989); p. 4766 - 4776 ; (from Gmelin) View in Reaxys

(v5) (v5)(v5)(v5)

(v5)(v5) (v5) (v5)

Br Os

Br

(v8)

Br

Os

O O

O

(v3)

(v8)

O Br

(v3)

(v3)

(v3)

Rx-ID: 26368470 View in Reaxys 79/328 Yield

Conditions & References

39 %, 64 %

in dichloromethane-d2, (N2); electrophilic cleavage reaction by addn. of bromine to a soln. of Cp*Os(CO)2Et in CD2Cl2;; not isolated, detected by NMR; Johnston, Laura J.; Baird, Michael C.; Organometallics; vol. 7; (1988); p. 2469 - 2475 ; (from Gmelin) View in Reaxys

(v5) (v5) (v5) (v5)

(v5) (v5)(v5) (v5)

Br Os P

Br

(v8)

Br

Os

O (v4) (v3)

P

(v8)

O Br (v4) (v3)

Rx-ID: 26368487 View in Reaxys 80/328 Yield 65 %, 78 %

Conditions & References in dichloromethane-d2, (N2); electrophilic cleavage reaction by addn. of bromine to a soln. of Cp*Os(CO)(PMe2Ph)Et in CD2Cl2;; not isolated, detected by NMR; Johnston, Laura J.; Baird, Michael C.; Organometallics; vol. 7; (1988); p. 2469 - 2475 ; (from Gmelin) View in Reaxys

Br Br

Br HC

CH +2

Rx-ID: 1543759 View in Reaxys 81/328 Yield

Conditions & References With hydrogen, T= 100 °C , p= 60 - 720Torr , labelled with tritium; -ΔH; without hydrogen, Product distribution, Kinetics, Thermodynamic data

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Fornarini, Simonetta; Speranza, Maurizio; Journal of Physical Chemistry; vol. 91; nb. 8; (1987); p. 2154 - 2160 View in Reaxys

Br

Br

HC

Br

Br

CH +2

Rx-ID: 1543760 View in Reaxys 82/328 Yield

Conditions & References With hydrogen, T= 100 °C , p= 60 - 600Torr , labelled with tritium; -ΔH, Product distribution, Kinetics, Thermodynamic data Fornarini, Simonetta; Speranza, Maurizio; Journal of Physical Chemistry; vol. 91; nb. 8; (1987); p. 2154 - 2160 View in Reaxys O

O

O S

O

O Br

O

O

O

Br

O

O S

O

O

O

O

S O

Rx-ID: 1762533 View in Reaxys 83/328 Yield

Conditions & References Time= 20h, T= 85 - 90 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Baires, S. V.; Ivanov, V. B.; Vil'danova, L. T.; Ivanov, B. E.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 4; (1987); p. 879; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 4; (1987); p. 953 View in Reaxys Cl Cl

Br

Br

Rx-ID: 1894978 View in Reaxys 84/328 Yield

Conditions & References With bromine in gaseous matrix, T= 32 - 95 °C , Irradiation, analysis of the kinetic and thermochemical data of the competitive photobromination, Product distribution Tschuikow-Roux, E.; Salomon, D. R.; Journal of Physical Chemistry; vol. 91; nb. 3; (1987); p. 699 - 702 View in Reaxys S

S P S Br

S Br

S+

P

I–

S

S

Rx-ID: 2394184 View in Reaxys 85/328 Yield 50 %, 1.5 %, 46 %

Conditions & References Time= 4320h, T= 20 °C

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Kabachnik, M. I.; Pudovik, A. N.; Batyeva, E. S.; Al'fonsov, V. A.; Zamaletdinova, G. U.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 8; (1987); p. 1734 - 1737; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 8; (1987); p. 1871 - 1873 View in Reaxys

N

(v4)

O–

N

(v4) + (v4) N Co (v6) (v4)

O

Br

Br

Cl OO

N

Rx-ID: 26367459 View in Reaxys 86/328 Yield

Conditions & References in [D3]acetonitrile, Complex and allyl bromide was added to an NMR tube which contained CD3CN, after the soln. was degassed, the sealed NMR tube with a reflux condenser was thermostated at 353 K for 30 h;; Detected by NMR-spectroscopy at 298 K; the organic products were analysed by GLC; Ishikawa, Kunio; Fukuzumi, Shunichi; Tanaka, Toshio; Bulletin of the Chemical Society of Japan; vol. 60; nb. 2; (1987); p.

563 - 570 ; (from Gmelin) View in Reaxys

N

(v4)

O–

N

(v4) + (v4) N Co (v6) (v4)

O

Cl OO

Br

N

Br (v5) N (v4) Co + N (v4) N

Br

(v4)

O–

(v4)

N

O

Cl OO

Rx-ID: 26367462 View in Reaxys 87/328 Yield

Conditions & References in [D3]acetonitrile, Kinetics, Complex and PhCH2Br (molar ratio 1:1.4) was added to an NMR tube which contained CD3CN, after the soln. was degassed, the sealed NMR tube with a reflux condenser was thermostated at 353 K;; Detected by NMR-spectroscopy at 298 K; the organic products were analysed by GLC; Ishikawa, Kunio; Fukuzumi, Shunichi; Tanaka, Toshio; Bulletin of the Chemical Society of Japan; vol. 60; nb. 2; (1987); p.

563 - 570 ; (from Gmelin) View in Reaxys

N N

(v4)

(v4)Co + (v4) N (v6) (v4)

Br

Br

N

Rx-ID: 26586352 View in Reaxys 88/328 Yield

Conditions & References in [D3]acetonitrile, Complex and allyl bromide was added to an NMR tube which contained CD3CN, after the soln. was degassed, the sealed NMR tube with a reflux condenser was thermostated at 353 K for 30 h;; Detected by NMR-spectroscopy at 298 K; the organic products were analysed by GLC; Ishikawa, Kunio; Fukuzumi, Shunichi; Tanaka, Toshio; Bulletin of the Chemical Society of Japan; vol. 60; nb. 2; (1987); p.

563 - 570 ; (from Gmelin) View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

N

(v4)

N

+ (v4) (v4) N Co (v6) (v4)

Br

N

Br (v5)

Br

+ N Co (v4) N N (v4) N (v4) (v4)

Rx-ID: 26597532 View in Reaxys 89/328 Yield

Conditions & References in [D3]acetonitrile, Kinetics, Complex and PhCH2Br (molar ratio 1:1.4) was added to an NMR tube which contained CD3CN, after the soln. was degassed, the sealed NMR tube with a reflux condenser was thermostated at 353 K;; Detected by NMR-spectroscopy at 298 K; the organic products were analysed by GLC; Ishikawa, Kunio; Fukuzumi, Shunichi; Tanaka, Toshio; Bulletin of the Chemical Society of Japan; vol. 60; nb. 2; (1987); p.

563 - 570 ; (from Gmelin) View in Reaxys Cl

S

Cl

S P

S

S

Br

P

S

S

P S

Cl

S

S

Rx-ID: 1857620 View in Reaxys 90/328 Yield

Conditions & References

3.7 g, 5.8 g

With Bromotrichloromethane, Time= 18h, T= 100 - 110 °C , Yields of byproduct given Sinyashin, O.G.; Karimullin, Sh. A.; Kostin, V. P.; Batyeva, E. S.; Pudovik, A. N.; J. Gen. Chem. USSR (Engl. Transl.); vol.

56; nb. 8; (1986); p. 1700 - 1707,1505 - 1511 View in Reaxys

O

Br

Br Br

O

OH

O

Br

O O

O

Br

Br

Rx-ID: 1916698 View in Reaxys 91/328 Yield

Conditions & References With N,N-diethylaniline, Time= 2.5h, T= 98 °C , other bases, var. conditions, Product distribution Stalick, Wayne M.; Khorrami, Ali; Hatton, Kimi S.; Journal of Organic Chemistry; vol. 51; nb. 19; (1986); p. 3577 - 3581 View in Reaxys

I

Br

Br

I

Rx-ID: 2397926 View in Reaxys 92/328 Yield

Conditions & References With tetrabutylammomium bromide in nitromethane-d3, T= 25 °C , ΔG, Equilibrium constant, Thermodynamic data Bochkov, A. F.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 10; (1986); p. 1837 - 1848; Zhurnal Organicheskoi Khimii; vol. 22; nb. 10; (1986); p. 2050 - 2063

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys

I

Br

Br

I

Rx-ID: 2854387 View in Reaxys 93/328 Yield

Conditions & References With tetrabutylammomium bromide in nitromethane-d3, T= 25 °C , ΔG, Equilibrium constant, Thermodynamic data Bochkov, A. F.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 10; (1986); p. 1837 - 1848; Zhurnal Organicheskoi Khimii; vol. 22; nb. 10; (1986); p. 2050 - 2063 View in Reaxys

O

C

O

Br

O

O

Br

Br

O

O

Rx-ID: 2394325 View in Reaxys 94/328 Yield

Conditions & References

64 %, 32 %

With [(1,5-hexadiene)Rh(μ-Cl)]2, potassium iodide, T= 75 - 90 °C , p= 735.5Torr , overnight or in n-heptane Buchan, Caroline; Hamel, Nathalie; Woell, James B.; Alper, Howard; Tetrahedron Letters; vol. 26; nb. 47; (1985); p. 5743 5746 View in Reaxys

O

O

O

Br C

I

O

O

O

Rx-ID: 3885418 View in Reaxys 95/328 Yield

Conditions & References

42 % Chromat., 60 %

With [(1,5-hexadiene)Rh(μ-Cl)]2, potassium iodide, T= 150 °C , p= 14710.2Torr Buchan, Caroline; Hamel, Nathalie; Woell, James B.; Alper, Howard; Tetrahedron Letters; vol. 26; nb. 47; (1985); p. 5743 5746 View in Reaxys

O

F

Br

O

O Br

F

P O F

F F F F

F O

F

F

F

F

O

F

O

F F

F

O

P

O

O

O

F

F

O

F

P

F

O

F

F F

O

O

F F

P

F

F

F

F F

Rx-ID: 1853164 View in Reaxys 96/328 Yield

Conditions & References Time= 96h, T= 20 °C

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Volkonskii, A. Yu.; Mysov, E. I.; Rokhlin, E. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 6; (1984); p. 1246 - 1257; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 6; (1984); p. 1356 - 1367 View in Reaxys

O

O

Br

O

O

Br P

O O

O P

O

O

O

O

Rx-ID: 1853211 View in Reaxys 97/328 Yield

Conditions & References

61 %

Time= 1h, Heating, argon atmosphere Livantsov, M. V.; Proskurnina, M. V.; Prishchenko, A. A.; Lutsenko, I. F.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb.

11; (1984); p. 2504 - 2517,2237 - 2249 View in Reaxys S

S P

S

Br

S

S

S

S P

P S

Br

S

Rx-ID: 1857621 View in Reaxys 98/328 Yield

Conditions & References

37 %, 46 %, With bromine, Time= 0.5h, Ambient temperature, Product distribution 45 % Sinyashin, O. G.; Karimullin, Sh. A.; Pudovik, D. A.; Batyeva, E. S.; Pudovik, A. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 11; (1984); p. 2458 - 2463,2195 - 2199 View in Reaxys

Br

O O O

P

Br

P O

N

N N N

Rx-ID: 1935330 View in Reaxys 99/328 Yield

Conditions & References

67 %

in toluene, Time= 19h, gradually from RT to reflux Mairova, E. D.; Platonov, A. Yu.; Chistokletov, V. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 5; (1984); p. 1041 1045,929 - 932 View in Reaxys

F

F F

O

O

O

F

Br

Br F

F

P

P

O

O

O

F

O

F F F

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

F F

F F

F O

O

O

F

F

F

F

F

P O

F

P

O

F F

F

O

F

F

O

F

O

Br

F

F

F

F F

F

O

F

F F

Rx-ID: 1948128 View in Reaxys 100/328 Yield

Conditions & References

34.7 %

Time= 144h, T= 20 °C , p= 10Torr Volkonskii, A. Yu.; Mysov, E. I.; Rokhlin, E. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 6; (1984); p. 1246 - 1257; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 6; (1984); p. 1356 - 1367 View in Reaxys

O

Br

O

O O

O

P

O

O

Br

P

O

O

O

O O

Rx-ID: 1959970 View in Reaxys 101/328 Yield

Conditions & References

76 %

in toluene, Time= 12h, T= 60 - 100 °C Mairova, E. D.; Platonov, A. Yu.; Chistokletov, V. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 5; (1984); p. 1041 1045,929 - 932 View in Reaxys

O

F

O

O

F

P O

Br

F

F F F F F F

O

O

Br

F

O P

F

O O

F F

F

P O

F O

F

F F

F

Rx-ID: 1981559 View in Reaxys 102/328 Yield

Conditions & References Time= 11h, T= 90 - 100 °C Volkonskii, A. Yu.; Mysov, E. I.; Rokhlin, E. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 6; (1984); p. 1246 - 1257; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 6; (1984); p. 1356 - 1367 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

O

O P

N

O

N

O O Br

P

O

N N

Rx-ID: 1991188 View in Reaxys 103/328 Yield

Conditions & References

71 %

in benzene, 1) RT, 1 h, 2) gradually from RT to reflux Mairova, E. D.; Platonov, A. Yu.; Chistokletov, V. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 5; (1984); p. 1041 1045,929 - 932 View in Reaxys

Br

O

N

O O

P

Br

P O

N

N N

Rx-ID: 2016811 View in Reaxys 104/328 Yield

Conditions & References

67 %

in benzene, 1) RT, 1 h, 2) gradually from RT to reflux Mairova, E. D.; Platonov, A. Yu.; Chistokletov, V. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 5; (1984); p. 1041 1045,929 - 932 View in Reaxys

Br

O

N

O O

Br

P

Cl

P

Cl

O

N

N N

Rx-ID: 2019981 View in Reaxys 105/328 Yield 79 %

Conditions & References in benzene, 1) RT, 1 h, 2) gradually from RT to reflux Mairova, E. D.; Platonov, A. Yu.; Chistokletov, V. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 5; (1984); p. 1041 1045,929 - 932 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

O O O

O P

O

O

O

O

P

Br

O

O

O O

Rx-ID: 2046405 View in Reaxys 106/328 Yield

Conditions & References

79 %

in benzene, 1) RT, 1 h, 2) gradually from RT to reflux, 7.5 h Mairova, E. D.; Platonov, A. Yu.; Chistokletov, V. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 5; (1984); p. 1041 1045,929 - 932 View in Reaxys Br

O

Cl

O P

O

O

O O

O O

Cl P

Br

O

O

O O

Rx-ID: 2121178 View in Reaxys 107/328 Yield

Conditions & References

51 %

in benzene, 1) RT, 1 h, 2) gradually from RT to reflux Mairova, E. D.; Platonov, A. Yu.; Chistokletov, V. N.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 5; (1984); p. 1041 1045,929 - 932 View in Reaxys

F

F

Br F

O

P

O O

Br

Cl

Cl

O

Br P

F F

F

Rx-ID: 3778102 View in Reaxys 108/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References

72.3 %

in dichloromethane, Time= 28h, T= 50 °C Volkonskii, A. Yu.; Mysov, E. I.; Rokhlin, E. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; nb. 6; (1984); p. 1246 - 1257; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 6; (1984); p. 1356 - 1367 View in Reaxys

(v5) (v5)(v5) (v5)

(v4)

P

Rh

(v5)(v5) (v5) (v5)

Br

Rh Br

(v8)

Br

Br

(v8)

(v4)

P

Rx-ID: 26857433 View in Reaxys 109/328 Yield

Conditions & References With Br2 in not given, 25°C; Periana, Roy A.; Bergman, Robert G.; Organometallics; vol. 3; (1984); p. 508 - 510 ; (from Gmelin) View in Reaxys O

Br

O

O

Br

Br

O

O

Br O

O

Br O

O

O

Br

Br

Br

O

O

Rx-ID: 1510043 View in Reaxys 110/328 Yield

Conditions & References With dibenzoyl peroxide, Time= 0.5h, T= 90 °C , Product distribution Rol'nik, L. Z.; Kalashnikov, S. M.; Pastushenko, E. V.; Zlot-skii, S. S.; Rakhmankulov, D. L.; Journal of Organic Chemistry USSR (English Translation); vol. 18; (1982); p. 1296 - 1299; Zhurnal Organicheskoi Khimii; vol. 18; nb. 7; (1982); p. 1486 1489 View in Reaxys With dibenzoyl peroxide, Time= 2h, T= 100 °C , other temperature, other time, Rate constant, Product distribution Rol'nik, L. Z.; Pastushenko, E. V.; Zlot-skii, S. S.; Rakhmankulov, D. L.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb.

10; (1983); p. 2363 - 2367,2131 - 2134 View in Reaxys O O

O

Br

Br O

O

O

Br

Br

Br

O

O

O

O

O

Br

Br

Br

O

Rx-ID: 1515685 View in Reaxys 111/328 Yield 60 %

Conditions & References With dibenzoyl peroxide, Time= 2h, T= 100 °C , other temperature, Rate constant, Product distribution Rol'nik, L. Z.; Pastushenko, E. V.; Zlot-skii, S. S.; Rakhmankulov, D. L.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb.

10; (1983); p. 2363 - 2367,2131 - 2134 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

2H

N

2H

O

O P+

Br– 2

2

H

H

O Cl

2

H Cl

O–

Br

O

P

2H

2H

N+

N+

2H

Br–

O 2H

2H

2H 2H

2H

2H 2H

Rx-ID: 1648084 View in Reaxys 112/328 Yield

Conditions & References in chloroform-d1, Time= 0.0166667h, T= 30 °C Thuong, Nguyen Thanh; Barbier, Christine; Asseline, Ulysse; Phosphorus and Sulfur and the Related Elements; vol. 14; (1983); p. 357 - 366 View in Reaxys

O

O

Si

N Si

O

O

Br

P O

N

Br

P

Si O

O

O

Rx-ID: 1904663 View in Reaxys 113/328 Yield

Conditions & References

70 %, 73 %

Time= 0.666667h, T= 120 - 125 °C Kozhushko, B. N.; Lomakina, A. V.; Paliichuk, Yu. A.; Shokol, V. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 9; (1983); p. 1960 - 1967,1768 - 1774 View in Reaxys

Br

O Br

O

O

O

Rx-ID: 2206254 View in Reaxys 114/328 Yield

Conditions & References Time= 2h, T= 150 - 160 °C Cornejo, Jaime J.; Ghodsi, Shahram; Johnson, R. Douglas; Woodling, Rick; Rickburn, Bruce; Journal of Organic Chemistry; vol. 48; nb. 21; (1983); p. 3869 - 3876 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

I

Br

I

Rx-ID: 2851794 View in Reaxys 115/328 Yield

Conditions & References With aluminum oxide, tetrabutyl phosphonium bromide in gas, T= 150 °C , p= 760Torr , effect of catalytic bed, Product distribution Tundo, Pietro; Venturello, Paolo; Angeletti, Enrico; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1983); p. 485 - 492 View in Reaxys

O

O P O

Br– P+ Br

F F

O

O

Br

Br

P P

O F

F

Rx-ID: 3875071 View in Reaxys 116/328 Yield

Conditions & References

92 %, 65 %

in dichloromethane, Time= 0.166667h, Ambient temperature, Product distribution, Mechanism Burton, Donald J.; Naae, Douglas, G.; Flynn, Richard M.; Smart, Bruce E.; Brittelli, David R.; Journal of Organic Chemistry; vol. 48; nb. 20; (1983); p. 3616 - 3618 View in Reaxys

F

F

F

F

F

F Tl

F

F

Ge

FF

F

Br

F

BrTl F

F F F

F FF

F

Br

Br Br Ge

F

Br

F

F F

F

Rx-ID: 27056204 View in Reaxys 117/328 Yield

Conditions & References

86 %, 100 %, 94 %

in hexane, under N2, to suspn. of germyl-thallium compound in hexane added in small portions of 5percent soln. of Br2 in hexane Bochkarev, M.N.; Basalgina, T.A.; Kalinina, G.S.; Razuvaev, G. A.; Journal of Organometallic Chemistry; vol. 243; nb. 4; (1983); p. 405 - 410 ; (from Gmelin) View in Reaxys

Cl Br

Rx-ID: 1896860 View in Reaxys 118/328 Yield

Conditions & References With Cu(EtBr)2+, free energie for exchange of both ligands, Thermodynamic data Jones, Roger W.; Staley, Ralph H.; Journal of the American Chemical Society; vol. 104; nb. 8; (1982); p. 2296 - 2300

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys

Br

O

Br

Br

O

O H Br

O

O O

Rx-ID: 1903157 View in Reaxys 119/328 Yield

Conditions & References With di-tert-butyl peroxide, Time= 0.5h, T= 130 °C , Mechanism Rol'nik, L. Z.; Kalashnikov, S. M.; Pastushenko, E. V.; Zlotskii, S. S.; Rakhmankulov, D. L.; J. Appl. Chem. USSR (Engl.

Transl.); vol. 55; nb. 10; (1982); p. 2383 - 2384,2185 - 2186 View in Reaxys

Br

Br

Rx-ID: 2855930 View in Reaxys 120/328 Yield

Conditions & References With Cu(EtBr)2+, free energie for exchange of both ligands, Thermodynamic data Jones, Roger W.; Staley, Ralph H.; Journal of the American Chemical Society; vol. 104; nb. 8; (1982); p. 2296 - 2300 View in Reaxys O

O O

O

O P

O

Br

O

O P O

O

Br

Rx-ID: 3874448 View in Reaxys 121/328 Yield

Conditions & References

90 %

Time= 2h, T= 90 - 95 °C Boeckman, Robert K.; Ko, Soo Sung; Journal of the American Chemical Society; vol. 104; nb. 4; (1982); p. 1033 - 1041 View in Reaxys

Br

O Si

P O

O

Rx-ID: 3877203 View in Reaxys 122/328 Yield 89 %

Conditions & References With bromine, Ambient temperature Gazizov, T. Kh.; Sudarev, Yu. I.; Shakirov, I. Kh.; Smirnov, V. N.; Pudovik, A. N.; J. Gen. Chem. USSR (Engl. Transl.); vol.

52; nb. 4; (1982); p. 769 - 776,667 - 673

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys O

O

Br

O

Br O

O

Br

O

O

Br

O

O

Br O

O

O

Br

O O

O

Rx-ID: 4146247 View in Reaxys 123/328 Yield

Conditions & References With dibenzoyl peroxide, T= 79.9 °C , var. temperatures; relation of the initial rate of formation to the concentration of the ortho ester, Product distribution, Mechanism Rol'nik, L. Z.; Kalashnikov, S. M.; Pastushenko, E. V.; Zlot-skii, S. S.; Rakhmankulov, D. L.; J. Gen. Chem. USSR (Engl.

Transl.); vol. 52; nb. 9; (1982); p. 2126 - 2132,1893 - 1898 View in Reaxys

Br

Al

Rx-ID: 25060065 View in Reaxys 124/328 Yield

Conditions & References 1 : EXAMPLE 1 EXAMPLE 1 Triethylaluminum was reacted with an excess of methyl bromide using a catalyst comprising a mixture of ethyl iodide-vanadium oxytrichloride-triethylaluminum or ethyl iodide-vanadium oxytrichloride-trimethylaluminum.

The reactions were carried out at 75° C. for 16 hours and at 75° C. for five hours, respectively.

Yields of ethyl bromide and trimethylaluminum were ~85 percent.

Patent; Ethyl Corporation; US4364873; (1982); (A) English View in Reaxys 5 : EXAMPLE 5 EXAMPLE 5 Triethylaluminum was reacted with methyl bromide at 75° C. in the presence of ethyl iodide-vanadium oxytrichloride-triethylaluminum catalyst mixture.

After 1.5 hours, about 20 percent trimethylaluminum was formed.

After 22 hours, the exchange was almost complete.

Yields of ethyl bromide and trimethylaluminum were 80-85 percent (by NMR).

Patent; Ethyl Corporation; US4364873; (1982); (A) English View in Reaxys 8 : EXAMPLE 8 EXAMPLE 8 Using a catalyst mixture comprising 6-25 mmoles of ethyl iodide per 21.9 mmoles of triethylaluminum and one mmole vanadium oxytrichloride, methyl bromide was reacted with triethylaluminum at 75° C. for about 20 hours to produce effective yields of ethyl bromide and trimethylaluminum.

Patent; Ethyl Corporation; US4364873; (1982); (A) English View in Reaxys O

O Br

Si

O

O

O

O

Rx-ID: 3349893 View in Reaxys 125/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References

92 %

With chloro-trimethyl-silane, sodium bromide, Time= 2h, Heating, Me3SiBr generated in situ, Product distribution Schmidt, Arthur H.; Russ, Manuel; Chemische Berichte; vol. 114; nb. 3; (1981); p. 1099 - 1110 View in Reaxys O O

O

O P Br

O

O

O

O P

Br

O

O

Rx-ID: 3536580 View in Reaxys 126/328 Yield

Conditions & References 1) 142-145 deg C, 4h, 2) 165-168 deg C, 1h, Yield given. Multistep reaction. Yields of byproduct given Varlet, J. M.; Fabre, G.; Sauveur, F.; Collignon, N.; Savignac, Ph.; Tetrahedron; vol. 37; (1981); p. 1377 - 1384 View in Reaxys

O Br

Br

P

P O

Rx-ID: 3565831 View in Reaxys 127/328 Yield

Conditions & References Karsch, Hans H.; Phosphorus and Sulfur and the Related Elements; vol. 12; (1981); p. 217 - 226 View in Reaxys O

O P

Br

O

O Br

O P O

Rx-ID: 3874575 View in Reaxys 128/328 Yield

Conditions & References Wozniak, Michel; Nowogrocki, Guy; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1981); p. 2423 - 2428 View in Reaxys

Br

O

O

O

Br P O

P

O

O

Br

Br

Rx-ID: 2151110 View in Reaxys 129/328 Yield

Conditions & References T= -50 °C Michalski, Jan; Pakulski, Marek; Skowronska, Aleksandra; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 833 - 836 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br Br–

N+

Rx-ID: 2637587 View in Reaxys 130/328 Yield

Conditions & References

33 %

With 2,4,6-triphenylpyridine, T= 180 - 220 °C , p= 0.5 - 2Torr Katritzky, Alan R.; Al-Omran, Fatima; Patel, Ranjan C.; Thind, Sukhpal S.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1890 - 1894 View in Reaxys

Br

N+

Br–

Rx-ID: 3017878 View in Reaxys 131/328 Yield

Conditions & References

50 %

With 2,4,6-triphenylpyridine, T= 180 - 220 °C , p= 0.5 - 2Torr Katritzky, Alan R.; Al-Omran, Fatima; Patel, Ranjan C.; Thind, Sukhpal S.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1890 - 1894 View in Reaxys

Cl

Br

Br– N+

Rx-ID: 3023953 View in Reaxys 132/328 Yield 97 %

Conditions & References With 2,4,6-triphenylpyridine, T= 180 - 220 °C , p= 0.5 - 1.5Torr Katritzky, Alan R.; Al-Omran, Fatima; Patel, Ranjan C.; Thind, Sukhpal S.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 1890 - 1894 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

4-(diethoxyphosphinyl)-2(Z,E)-3-(trifluoromethyl)crotonic acid ethyl ester Rx-ID: 25283401 View in Reaxys 133/328

Yield

Conditions & References 31 : 4-(diethoxyphosphinyl)-2(Z,E)-3-(trifluoromethyl)-crotonic acid ethyl ester EXAMPLE 31 4-(diethoxyphosphinyl)-2(Z,E)-3-(trifluoromethyl)-crotonic acid ethyl ester Ethyl-3-trifluoromethyl-4-bromo-2(Z,E)-butenoate (18.48 g., 70.7 mmol) and 12.95 g. (78 mmol) of triethylphosphite were heated at 140° C. for 3.0 hrs. while the ethyl bromide formed during the reaction was distilled off.

The resulting crude product was distilled using a Vigreux column at 1 mm. to yield a colorless liquid, b.p. 105°-110° C. containing a 1:1 mixture of isomers including 4-diethoxyphosphinyl)-2(Z,E)-3-(trifluoromethyl)-crotonic acid ethyl ester and a bp 110°-113° C. mixture of the same isomers.

Patent; Hoffmann-La Roche Inc.; US4169100; (1979); (A) English View in Reaxys Br

2-cyano-2-ethoxyimino-N-(3'-methoxypropyl)carbamoylacetamide Rx-ID: 25212303 View in Reaxys 134/328 Yield

Conditions & References 4 : EXAMPLE 4 EXAMPLE 4 According to the method of Example 2, reacting 2-cyano-2-hydroxyimino-N-(3'-methoxypropyl)carbamoylacetamide with ethyl bromide, 2-cyano-2-ethoxyimino-N-(3'-methoxypropyl)carbamoylacetamide can be prepared.

Patent; E. I. Du Pont de Nemours and Company; US3979518; (1976); (A) English View in Reaxys

O

O

Br

Br

Sn

N

N

Sn

O

O

Rx-ID: 26487706 View in Reaxys 135/328 Yield

Conditions & References Kinetics Davies, A. G.; Roberts, B. P.; Smith, J. M.; J. Chem. Soc. Perkin Trans. II; (1972); p. 2221 - 2224 View in Reaxys vol. Sn: Org.Verb.1; 1.1.1.2.4.7, page 73 - 76 ; (from Gmelin) View in Reaxys

Br Br

Br

Sb

Sb Br

Rx-ID: 26599253 View in Reaxys 136/328 Yield 84 %

Conditions & References at 400 Torr, 60 min, at 220-240°C, vac. distn.

Besolova, E. A.; Foss, V. L.; Lutsenko, I. F.; Zhurnal Obshchei Khimii; vol. 38; (1968); p. 270 - 275; Zhurnal Obshchei Khimii; vol. 38; (1968); p. 267 - 273 View in Reaxys vol. Sb: Org.Comp.2; 1.2.1.1.5.1, page 20 - 24 ; (from Gmelin) View in Reaxys

78 %

at 400 Torr, 60 min, at 220-240°C, vac. distn.

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Hartmann, H.; Kuehl, G.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 312; (1961); p. 186 - 194 ; (from Gmelin) View in Reaxys 78 %

at 400 Torr, 60 min, at 220-240°C, vac. distn. vol. Sb: Org.Comp.2; 1.2.1.1.5.1, page 20 - 24 ; (from Gmelin) View in Reaxys

75 %

at 450 Torr, 40-50 min, at 190-210°C, vac. distn.

Issleib, K.; Hamann, B.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 339; (1965); p. 289 - 297 ; (from Gmelin) View in Reaxys

75 %

at 450 Torr, 40-50 min, at 190-210°C, vac. distn. vol. Sb: Org.Comp.2; 1.2.1.1.5.1, page 20 - 24 ; (from Gmelin) View in Reaxys

63 %

at 400-410 Torr, at 170-180°C, vac. distn.

Davies, A. G.; Hook, S. C. W.; Journal of the Chemical Society [Section] C: Organic; (1971); p. 1660 - 1665 ; (from Gmelin) View in Reaxys

63 %

at 400-410 Torr, at 170-180°C, vac. distn. vol. Sb: Org.Comp.2; 1.2.1.1.5.1, page 20 - 24 ; (from Gmelin) View in Reaxys

N Br

Sn

N

Br

N

Sn

N

N N

Rx-ID: 26436878 View in Reaxys 137/328 Yield

Conditions & References Koehler, H.; Muelmann, E. v.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 373; (1970); p. 222 - 229 View in Reaxys vol. Sn: Org.Verb.1; 1.1.1.2.4.7, page 73 - 76 ; (from Gmelin) View in Reaxys

Br

Br

Br

Br

H

Br

H

Br

Rx-ID: 26433153 View in Reaxys 138/328 Yield

Conditions & References With hydrogen in neat (no solvent), Kinetics, reaction of CBr4 with H/H2 at 25-75°C and 0.002 Torr; mechanism dicussed; Cnotka, H.-G.; Martin, H.; Seidel, W.; Zeitschrift fuer Physikalische Chemie (Muenchen); vol. 65; (1969); p. 139 - 146 View in Reaxys vol. C: MVol.D2; 4.1.3.7.4, page 271 - 271 View in Reaxys Cnotka, H.-G.; Diss. Kiel 1962 ; (from Gmelin) View in Reaxys

Br

Br

Br

Sn

Br

Br

Br

Br

Sn Br BrBr

Rx-ID: 26770568 View in Reaxys 139/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References in not given Boue et al.; Tetrahedron Letters; (1968); p. 1047 View in Reaxys Boue, S.; Gielen, M.; Nasielski, J.; Lieutenant, J. P.; Spielmann, R.; Bulletin des Societes Chimiques Belges; vol. 78; (1969); p. 135 - 146 View in Reaxys vol. Sn: Org.Verb.3; 1.1.5.1, page 95 - 99 ; (from Gmelin) View in Reaxys O

O

Br

Br

HO

Br

O Br O

Rx-ID: 597184 View in Reaxys 140/328 Yield

Conditions & References Erhitzen des Reaktonsprodulkts unter 31 Torr Dull; Abend; Journal of the American Chemical Society; vol. 81; (1959); p. 2588,1589 View in Reaxys O

O P

Br

O

Br

Br

O

O

Br

H P

P O

O

O

O P

O

O

O

Rx-ID: 684014 View in Reaxys 141/328 Yield

Conditions & References T= 131 - 145 °C , Produkt 5: Aethylphosphonsaeure-diaethylester; Produkt 6: Aethandiyldiphosphonsaeure-tetraaethylester Garner et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 532,535 View in Reaxys

O

O Br

O

O

Br

NH 2

NH 2

Rx-ID: 751487 View in Reaxys 142/328 Yield

Conditions & References T= 175 °C Gompper; Christmann; Chemische Berichte; vol. 92; (1959); p. 1944,1948 View in Reaxys O

O P

Br

O O

O

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O Br

O O

P O

O O

O

Rx-ID: 835806 View in Reaxys 143/328 Yield

Conditions & References T= 137 °C Garner et al.; Journal of Organic Chemistry; vol. 24; (1959); p. 532,535 View in Reaxys

O

O Br

NH 2

Br

O

O

HO

N H

N

OH

N

N

cyanuric acid tribenzyl ester

OH

Rx-ID: 6212415 View in Reaxys 144/328 Yield

Conditions & References T= 145 °C Gompper; Christmann; Chemische Berichte; vol. 92; (1959); p. 1944,1948 View in Reaxys Br

<1-14C>-ethanol

phosphorus (III)-bromide Rx-ID: 6395481 View in Reaxys 145/328

Yield

Conditions & References With ethanol, Am C-Atom 1 mit Kohlenstoff-14 markiertes Bromaethan ist erhalten worden Hodnett; Gallagher; Journal of Organic Chemistry; vol. 24; (1959); p. 564 View in Reaxys

O

O Br

tritium containing lithium borate Rx-ID: 6395483 View in Reaxys 146/328 Yield

Conditions & References With tetrahydrofuran, anschliessend Behandeln mit wss.Bromwasserstoffsaeure;Bildung von Tritium enthaltendem Bromaethan Hodnett; Gallagher; Journal of Organic Chemistry; vol. 24; (1959); p. 564 View in Reaxys Br

Br

Br Br

Ta

Br

3

Br– (v2)

(v5)

O

3+Ta

O

Br

Rx-ID: 26344487 View in Reaxys 147/328 Yield

Conditions & References in diethyl ether, 74°C, in vac.

Fairbrother, A. M.; Cowley, A. H.; Scott, N.; Journal of the Less-Common Metals; vol. 1; (1959); p. 206 - 216 ; (from Gmelin) View in Reaxys in diethyl ether, 74°C, in vac.

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Cowley, A. H.; Fairbrother, F.; Scott, N.; Journal of the Chemical Society; (1958); p. 3133 - 3137 View in Reaxys vol. Ta: MVol.B1; 7, page 141 - 159 ; (from Gmelin) View in Reaxys

Br

(v3)

O Br TaBrBr Br (v6) Br

Rx-ID: 26649918 View in Reaxys 148/328 Yield

Conditions & References in neat (no solvent), byproducts: tantalum oxide bromide; decomposition in vacuum at 300 °C; Cowley, A. H.; Fairbrother, F.; Scott, N.; Journal of the Chemical Society; (1958); p. 3133 - 3137 View in Reaxys vol. Ta: MVol.B2; 163, page 372 - 374 ; (from Gmelin) View in Reaxys Br

bromo-80 containing aluminium bromide Rx-ID: 6395479 View in Reaxys 149/328 Yield

Conditions & References Bildung von Brom-80- enthaltendem Bromaethan Aditya; Willard; Journal of the American Chemical Society; vol. 79; (1957); p. 3367,3368 View in Reaxys O

O P

O N

O

Br

O

O

Br

O

isopropyliden-amidophosphoric acid diethyl ester

P O

O

Rx-ID: 6729219 View in Reaxys 150/328 Yield

Conditions & References Temperatur:55-60 degreeC. Allen; Journal of the American Chemical Society; vol. 79; (1957); p. 3071 View in Reaxys

Br

O

Br

H

Br

Rx-ID: 6800405 View in Reaxys 151/328 Yield

Conditions & References T= 26 °C Burwell; Fuller; Journal of the American Chemical Society; vol. 79; (1957); p. 2332,2334 View in Reaxys Br

Br

H

Br

Br

Rx-ID: 6801369 View in Reaxys 152/328 Yield

Conditions & References beim Beschuss mit Neutronen Levey; Willard; Journal of Chemical Physics; vol. 25; (1956); p. 904,907

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys Gordus; Willard; Journal of the American Chemical Society; vol. 79; (1957); p. 4609,4611,4612 View in Reaxys Br Br

Br

Br

Br

Rx-ID: 6801370 View in Reaxys 153/328 Yield

Conditions & References beim Beschuss mit Neutronen Levey; Willard; Journal of Chemical Physics; vol. 25; (1956); p. 904,907 View in Reaxys Gordus; Willard; Journal of the American Chemical Society; vol. 79; (1957); p. 4609,4611,4612 View in Reaxys Br

Br

Br Br

Br

Br

pumice stone

Br

Rx-ID: 7060995 View in Reaxys 154/328 Yield

Conditions & References T= 300 - 400 °C Mamedaliew; Guseinow; ; (1957); p. 57,63; ; (1959); p. 15949 View in Reaxys

H

O

O Br

O

O

Br

H

Rx-ID: 437660 View in Reaxys 155/328 Yield

Conditions & References T= 180 °C Weinstock; Journal of the American Chemical Society; vol. 78; (1956); p. 4967,4969 View in Reaxys

Br– 3

2

O–

OH

Br

O Br

O

Sb5+

O

Rx-ID: 628777 View in Reaxys 156/328 Yield

Conditions & References T= 130 - 135 °C Dubrowina; Uchenye Zapiski, Kazanskii Gosudarstvennyi Universitet; vol. 116; nb. 2; (1956); p. 3,16,39; ; (1957); p. 6534 View in Reaxys

O

Br

Ag+

bromo-82 containing bromine O–

Rx-ID: 6395480 View in Reaxys 157/328 Yield

Conditions & References With Trichloroethylene, Bildung von Brom-82-enthaltendem Bromaethan Sixma et al; Recueil des Travaux Chimiques des Pays-Bas; vol. 75; (1956); p. 127,133,139

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys Br

<1-14C>-ethanol

potassium bromide Rx-ID: 6395482 View in Reaxys 158/328

Yield

Conditions & References With ethanol, sulfuric acid, Am C-Atom 1 mit Kohlenstoff-14 markiertes Bromaethan ist erhalten worden Sixma; Hendriks; Recueil des Travaux Chimiques des Pays-Bas; vol. 75; (1956); p. 169,173,175,179 View in Reaxys

O

O

O

Br

Br

O O O

Rx-ID: 597170 View in Reaxys 159/328 Yield

Conditions & References Kundiger; Richardson; Journal of the American Chemical Society; vol. 77; (1955); p. 2897 View in Reaxys Br O

Br

O

O

O O Br

Rx-ID: 222948 View in Reaxys 160/328 Yield

Conditions & References T= 145 °C McElvain; Stammer; Journal of the American Chemical Society; vol. 75; (1953); p. 2154,2158 View in Reaxys O O

Br

Br O

Br

Rx-ID: 228852 View in Reaxys 161/328 Yield

Conditions & References With phosphorus, bromine Klosa; Archiv der Pharmazie (Weinheim, Germany); vol. 286; (1953); p. 108,110 View in Reaxys Patent; Knoll A.G.; DE831239; (1950); View in Reaxys

O O

Br

O Br

O Br

Br

Br

Rx-ID: 234591 View in Reaxys 162/328 Yield

Conditions & References T= 185 °C , Pyrolysis McElvain; Stammer; Journal of the American Chemical Society; vol. 75; (1953); p. 2154,2158 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

H O Br

Br

Br

O

red phosphorus

Br

O

Br

Rx-ID: 5801638 View in Reaxys 163/328 Yield

Conditions & References Klosa; Archiv der Pharmazie (Weinheim, Germany); vol. 286; (1953); p. 108,110 View in Reaxys O O

Br

Br

Br

red phosphorus

Br

O

Br

Rx-ID: 5803592 View in Reaxys 164/328 Yield

Conditions & References Klosa; Archiv der Pharmazie (Weinheim, Germany); vol. 286; (1953); p. 108,110 View in Reaxys N Cl

Si O

Br

H

Br

Br

octamethyl-cyclo tetrasilicate Rx-ID: 7083515 View in Reaxys 165/328 Yield

Conditions & References Kumada; Hattori; Kogyo Kagaku Zasshi; vol. 56; (1953); p. 269; ; (1954); p. 10543 View in Reaxys

O

O

Br

O

O Br

O

O

O

O

Rx-ID: 573389 View in Reaxys 166/328 Yield

Conditions & References T= 125 - 140 °C , Produkt 5: 2-Benzyl-3-phenyl-propionsaeure-aethylester McElvain; McShane; Journal of the American Chemical Society; vol. 74; (1952); p. 2662,2666 View in Reaxys

Cl

Cl

O Br

Cl

Cl

Br

O

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

O

O

O

O Br

Br O

O

Rx-ID: 7064865 View in Reaxys 167/328 Yield

Conditions & References McElvain; Davie; Journal of the American Chemical Society; vol. 74; (1952); p. 1816,1818 View in Reaxys

O

Br

H N

O

O

H N

Br

O

Rx-ID: 174152 View in Reaxys 168/328 Yield

Conditions & References T= 130 °C Ben-Ishai; Katchalski; Journal of Organic Chemistry; vol. 16; (1951); p. 1025,1026 View in Reaxys

O

Br

O

N

Br

N O

O

Rx-ID: 174153 View in Reaxys 169/328 Yield

Conditions & References T= 130 °C Ben-Ishai; Katchalski; Journal of Organic Chemistry; vol. 16; (1951); p. 1025,1026 View in Reaxys O

O

O O

Br

N

N

Br

Rx-ID: 174201 View in Reaxys 170/328 Yield

Conditions & References Ben-Ishai; Katchalski; Journal of Organic Chemistry; vol. 16; (1951); p. 1025,1026 View in Reaxys O

Br

Br

O P

O

Br

H

O

Br

P

O

O

Br

P O

O

O

Rx-ID: 835836 View in Reaxys 171/328 Yield

Conditions & References Kamai; Doklady Akademii Nauk SSSR; vol. 79; (1951); p. 795,797; ; (1952); p. 6081 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Cl

Cl

O

hydrobromide of acetimidic acid ethyl ester Cl

O

O

O

O

Br

Rx-ID: 5853939 View in Reaxys 172/328 Yield

Conditions & References T= 25 °C , Kinetics McElvain; Tate; Journal of the American Chemical Society; vol. 73; (1951); p. 2233,2234 View in Reaxys

O

Br

O

O

NH 2

Br

H N

O

O

acetamide hydrobromide O

Rx-ID: 6209246 View in Reaxys 173/328 Yield

Conditions & References Ben-Ishai; Katchalski; Journal of Organic Chemistry; vol. 16; (1951); p. 1025,1026 View in Reaxys

Br

O Br

H

O

H O

Rx-ID: 7058094 View in Reaxys 174/328 Yield

Conditions & References bei langsamer Destillation unter Normaldruck Schostakowski; Bogdanowa; Zhurnal Obshchei Khimii; vol. 21; (1951); p. 388,392; engl. Ausg. S. 429 View in Reaxys Br

Rx-ID: 209128 View in Reaxys 175/328 Yield

Conditions & References With aluminum tri-bromide, hydrogen bromide, T= -78 °C Tulleners; Tuyn; Waterman; Recueil des Travaux Chimiques des Pays-Bas; vol. 53; (1934); p. 549 View in Reaxys With hydrogen bromide, silica gel, zinc dibromide, T= 50 °C Patent; I.G.Farbenind.; US2094064; (1935) View in Reaxys With hydrogen bromide, Unter der Einwirkung von stillen elektrischen Entladungen Patent; Shell Devel.Co.; US2672439; (1950) View in Reaxys Patent; N.V. de Bataafsche Petr.Mij.; DE846692; (1950); View in Reaxys With hydrogen bromide, T= 20 °C , ueber eine Mischung aus Asbest und Wismuttribromid Patent; Wibaut; DE445981; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 15; p. 364 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

With aluminum tri-bromide, hydrogen bromide, T= 0 °C Gustavson; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 16; (1884); p. 95 View in Reaxys O

O P

Br Si

O

Br

ethylphosphonic acid ethyl ester-triethylsilyl ester

ethylphosphonic acid bis-triethylsilyl ester Rx-ID: 6728258 View in Reaxys 176/328

Yield

Conditions & References T= 150 °C Malatesta; Gazzetta Chimica Italiana; vol. 80; (1950); p. 527,529,530 View in Reaxys Cl

Br

Cl

Br Br

Br

Br

O

O

Br

Cl

Rx-ID: 6800406 View in Reaxys 177/328 Yield

Conditions & References Katzl; Schubert; Monatshefte fuer Chemie; vol. 81; (1950); p. 988 View in Reaxys Br Br

N N

2H

Rx-ID: 14488 View in Reaxys 178/328 Yield

Conditions & References With diethyl ether, sulfuric acid, water-d2, und Kochen des entstandenen 1-Deutero-aethanols mit Bromwasserstoffsaeure Langseth; Bak; ; vol. 24; nb. 3; (1947); p. 15; ; (1948); p. 459 View in Reaxys O

O Cl

Br

Cl

Br

Cl

O

O

Sn ClCl

Rx-ID: 7044305 View in Reaxys 179/328 Yield

Conditions & References Smorgonskii; Zhurnal Obshchei Khimii; vol. 17; (1947); p. 416,418; ; (1948); p. 858 View in Reaxys

Cl

O Br

Cl

O

Rx-ID: 552969 View in Reaxys 180/328 Yield

Conditions & References With aluminum tri-bromide, anfangs unter Kuehlung, dann bei 35grad Korschak; Kolesnikow; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 437; ; (1945); p. 4595 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O O

O Br

O

O Br

O

O

O

Rx-ID: 597133 View in Reaxys 181/328 Yield

Conditions & References T= 125 °C McElvain; Engelhardt; Journal of the American Chemical Society; vol. 66; (1944); p. 1077,1082 View in Reaxys O

O P Br

Br

O

Rx-ID: 835839 View in Reaxys 182/328 Yield

Conditions & References T= 133 °C , Geschwindigkeit Kosolapoff; Journal of the American Chemical Society; vol. 66; (1944); p. 110 View in Reaxys T= 150 °C , Geschwindigkeit Kosolapoff; Journal of the American Chemical Society; vol. 66; (1944); p. 110 View in Reaxys

Br

Cl

O Br

Al

Cl

Br

O

Br

Rx-ID: 5462770 View in Reaxys 183/328 Yield

Conditions & References T= 35 °C Korschak; Kolesnikow; Zhurnal Obshchei Khimii; vol. 14; (1944); p. 437; ; (1945); p. 4595 View in Reaxys O

Mg

Br

Br

O

Cl

S Cl

Rx-ID: 733726 View in Reaxys 184/328 Yield

Conditions & References With dibutyl ether Cleveland; Murray; Journal of Chemical Physics; vol. 11; (1943); p. 452; Journal of Chemical Physics; vol. 12; (1944); p. 320 View in Reaxys

O

Br

O

O

Br

O

O Si

O

O

Rx-ID: 140350 View in Reaxys 185/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References T= 185 °C , reagiert analog mit Benzoylbromid Post; Norton; Journal of Organic Chemistry; vol. 7; (1942); p. 530 View in Reaxys O

O

Br

O

Br

O

O

O

Rx-ID: 573386 View in Reaxys 186/328 Yield

Conditions & References T= 120 - 125 °C McElvain; Kundiger; Journal of the American Chemical Society; vol. 64; (1942); p. 254,259 View in Reaxys O

O

Br

O

O

Br

O

O

Rx-ID: 597114 View in Reaxys 187/328 Yield

Conditions & References T= 250 °C , unter Druck McElvain; Kundiger; Journal of the American Chemical Society; vol. 64; (1942); p. 254,259 View in Reaxys

O O

O Br

Br

Br

OH

Br

H

O

H O

O

Br

Rx-ID: 5817626 View in Reaxys 188/328 Yield

Conditions & References T= 80 °C McElvain; Walters; Journal of the American Chemical Society; vol. 64; (1942); p. 1964 View in Reaxys

OH

Br

O

O

Br

H

Si O

O

Rx-ID: 6672375 View in Reaxys 189/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References T= 25 °C Post; Norton; Journal of Organic Chemistry; vol. 7; (1942); p. 530 View in Reaxys O

O

Br

N

Br

O

Br

O

Rx-ID: 7059011 View in Reaxys 190/328 Yield

Conditions & References und anschliessenden kurzen Erwaermen auf 67grad Dangjan; Danieljan; ; nb. 8; (1942); p. 23; ; (1946); p. 3395 View in Reaxys

Br

Br

H

Br

Br

oxygen

OH

Br

Rx-ID: 7065531 View in Reaxys 191/328 Yield

Conditions & References im UV-Licht Rust; Vaughan; Journal of Organic Chemistry; vol. 7; (1942); p. 495 View in Reaxys OH

Br Br

Br

Rx-ID: 6800398 View in Reaxys 192/328 Yield

Conditions & References Dangjan; Zhurnal Obshchei Khimii; vol. 11; p. 318; ; (1941); p. 5858 View in Reaxys O

O

lanthanum bromide

Br

lanthanum benzoate Rx-ID: 7455012 View in Reaxys 193/328 Yield

Conditions & References T= 154 °C Young; Arch; Shyne; Journal of the American Chemical Society; vol. 63; (1941); p. 957 View in Reaxys O

O

neodymium bromide

Br

neodymium benzoate Rx-ID: 7456007 View in Reaxys 194/328 Yield

Conditions & References T= 154 °C

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Young; Arch; Shyne; Journal of the American Chemical Society; vol. 63; (1941); p. 957 View in Reaxys Cl Al

Cl

Cl

ethyl bromide (2 mol)

Cl

Cl Br

Cl

Br

chlorobromoethane

Br

Rx-ID: 6211400 View in Reaxys 195/328 Yield

Conditions & References T= 25 °C , waehrend 14 Tagen Calingaert et al.; Journal of the American Chemical Society; vol. 62; (1940); p. 1546 View in Reaxys T= 115 °C , waehrend 20 h Calingaert et al.; Journal of the American Chemical Society; vol. 62; (1940); p. 1546 View in Reaxys

Cl Cl

Al

Br

Br

Cl

Cl

Br

Br

Cl

Cl

Cl

Rx-ID: 7060991 View in Reaxys 196/328 Yield

Conditions & References T= 25 °C , Gleichgewicht der Reaktion Calingaert et al.; Journal of the American Chemical Society; vol. 62; (1940); p. 1546 View in Reaxys

Br

Br Br

O O O

O

Rx-ID: 256307 View in Reaxys 197/328 Yield

Conditions & References Spaltet beim Destillieren unter vermindertem Druck Marvel; Cowan; Journal of the American Chemical Society; vol. 61; (1939); p. 3158 View in Reaxys

Br

Br

Br

Br

Sn

Sn

Sn

Rx-ID: 26488751 View in Reaxys 198/328 Yield

Conditions & References With bromine, at room temp.

Frankland, E.; Liebigs Annalen der Chemie; vol. 85; (1853); p. 329 - 373 View in Reaxys vol. Sn: Org.Verb.1; 1.1.1.2.4.6, page 72 - 73 ; (from Gmelin) View in Reaxys With bromine, at room temp.

Harada, T.; Sci. Papers Inst. Phys. Chem. Res. (Tokyo); vol. 35; (1939); p. 290 - 329 ; (from Gmelin)

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

View in Reaxys O

Cl

O

Cl Br

Cl

Br

Cl Br

Br

Br

O

Br

O

Br

Br

O

O Br

Br

Br

O

O

Br O

O

Rx-ID: 6987303 View in Reaxys 199/328 Yield

Conditions & References T= 0 - 5 °C , Produkt5: 4.4-Dibrom-3.3-diaethoxy-buttersaeure-aethylester Magnani; McElvain; Journal of the American Chemical Society; vol. 60; (1938); p. 2212 View in Reaxys Br O

Br

O

Br

zinc O

O

O

O

Rx-ID: 7059329 View in Reaxys 200/328 Yield

Conditions & References T= 160 °C Beyerstedt; McElvain; Journal of the American Chemical Society; vol. 59; (1937); p. 1274 View in Reaxys

B

bromoal <1mol>

Br

Br

O

Br

Br

B

diethylboronynoic acid <2.2-dibromo-vinyl ester

Rx-ID: 7074024 View in Reaxys 201/328 Yield

Conditions & References T= 90 °C Meerwein et al.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1937); p. 226,248 View in Reaxys Br Br

Br

O B

O

Br

Br

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

Br O

Br

Br

O B

ethylborononoic acid <2.2.2-tribromo-ethyl ester><2.2-dibromo-vinyl ester>

Br

Rx-ID: 7075660 View in Reaxys 202/328 Yield

Conditions & References Meerwein et al.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1937); p. 226,248 View in Reaxys Br Br

Br

Br

O

Br

Br

B

O Br

ethylborononoic acid <2.2.2-tribromo-ethyl ester><2.2-dibromo-vinyl ester>

ethylborononoic acid bis-<2.2.2-tribromo-ethyl ester> Rx-ID: 7075661 View in Reaxys 203/328

Yield

Conditions & References T= 135 °C Meerwein et al.; Journal fuer Praktische Chemie (Leipzig); vol. <2> 147; (1937); p. 226,248 View in Reaxys Cl

Br

Rx-ID: 209466 View in Reaxys 204/328 Yield

Conditions & References With aluminum tri-bromide, in Aethylbromid-Loesung Patent; Dow Chem.Co.; US2120675; (1936) View in Reaxys With aluminum tri-bromide Pouret; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 130; (1900); p. 1192; Bulletin de la Societe Chimique de France; vol. <3>25; (1901); p. 193 View in Reaxys Patent; Dow Chem.Co.; US1891415; (1930) View in Reaxys

O

Br

O O

Br

O

O

Br

O

O

ethylene glycol-ethyl ether-acetate

Rx-ID: 7075745 View in Reaxys 205/328 Yield

Conditions & References T= 110 °C Berggardh; ; vol. 44; (1935); p. 78; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 2267 View in Reaxys

H

H

Br Tl

Br

Tl

O

Br

Br

Rx-ID: 8251536 View in Reaxys 206/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References Melnikow; Gratschewa; Zhurnal Obshchei Khimii; vol. 5; (1935); p. 1786,1787; Chem. Zentralbl.; vol. 107; nb. I; (1936); p.

4554 View in Reaxys

Br

O Br

S

SO2

O

Rx-ID: 7086546 View in Reaxys 207/328 Yield

Conditions & References T= 25 °C Carre; Libermann; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 197; (1933); p. 1327; Bulletin de la Societe Chimique de France; vol. <5>1; (1934); p. 546 View in Reaxys Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 198; (1934); p. 182; Bulletin de la Societe Chimique de France; vol. <5>1; (1934); p. 743 View in Reaxys N

Br

O Br

S

SO2 O

Rx-ID: 7086547 View in Reaxys 208/328 Yield

Conditions & References T= 13 - 14 °C Carre; Libermann; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 197; (1933); p. 1327; Bulletin de la Societe Chimique de France; vol. <5>1; (1934); p. 546 View in Reaxys Carre; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 198; (1934); p. 182; Bulletin de la Societe Chimique de France; vol. <5>1; (1934); p. 743 View in Reaxys -1 Br

Br

(v4)

Br

Au BrBr

AuBr

(v2) +

Au

Rx-ID: 8268788 View in Reaxys 209/328 Yield

Conditions & References Burawoy; Gibson; Journal of the Chemical Society; (1934); p. 862,863 View in Reaxys

O

O Br–

S O

O–

O

O

Mg2+

Br

magnesium dibutylate

magnesium ethyl sulfate Rx-ID: 8279709 View in Reaxys 210/328

Yield

Conditions & References T= 85 - 95 °C Cope; Journal of the American Chemical Society; vol. 56; (1934); p. 1342,1345 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

O

Br

O

O O

Br

O

O

O Br

O

O

Rx-ID: 174214 View in Reaxys 211/328 Yield

Conditions & References T= 130 °C Berggardh; ; vol. 42; (1933); p. 76,77, 81; Chem. Zentralbl.; vol. 105; nb. I; (1934); p. 2267 View in Reaxys

O

O

Br

O

O

Br

O

O

O

O O

O Br

Rx-ID: 174215 View in Reaxys 212/328 Yield

Conditions & References T= 92 °C Berggardh; ; vol. 42; (1933); p. 76,80; Chem. Zentralbl.; vol. 105; nb. I; (1934); p. 2267 View in Reaxys

S Br

S

O

OH Br

Rx-ID: 459423 View in Reaxys 213/328 Yield

Conditions & References Beim Erhitzen mit Wasserdampf Krollpfeiffer; Mueller; Chemische Berichte; vol. 66; (1933); p. 739,742 View in Reaxys

Br Br

O

α-ethyl-butyrolactone-α-carboxylic acid ethyl ester

O

O

O

Rx-ID: 6800401 View in Reaxys 214/328 Yield

Conditions & References bei der Deestillation unter normalem Druck Cope; McElvain; Journal of the American Chemical Society; vol. 54; (1932); p. 4314 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

HN

NH 2

Rx-ID: 662793 View in Reaxys 215/328 Yield

Conditions & References T= 300 °C , beim Erhitzen des Hydrobromids Hickinbottom; Ryder; Journal of the Chemical Society; (1931); p. 1281,1286 View in Reaxys O

O

O

P

P

O

O

Br Br

Br

Rx-ID: 6800397 View in Reaxys 216/328 Yield

Conditions & References Arbusow; Arbusow; Journal fuer Praktische Chemie (Leipzig); vol. <2>130; (1931); p. 130; Zhurnal Obshchei Khimii; vol. 2; (1932); p. 366 View in Reaxys O

O Br

S O

O

Rx-ID: 102611 View in Reaxys 217/328 Yield

Conditions & References With ethanol, calcium bromide Koten; McMahon; ; vol. 19; nb. 5; p. 8; Chem. Zentralbl.; vol. 101; nb. II; (1930); p. 3388 View in Reaxys Br O

Rx-ID: 172044 View in Reaxys 218/328 Yield

Conditions & References With hydrogen bromide Underwood; Toone; Journal of the American Chemical Society; vol. 52; (1930); p. 393 View in Reaxys

O

Br

O O O

O Br

O

O

O Br

O

O

O O

Rx-ID: 174154 View in Reaxys 219/328 Yield

Conditions & References T= 190 °C Lyden; ; vol. 38; p. 68; Chem. Zentralbl.; vol. 101; nb. I; (1930); p. 3171 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

OH

Br

O

O O

Br

Br

PBr Br

α-ethoxycarbonyl-α-valerolactone

Br

O

Rx-ID: 6800404 View in Reaxys 220/328 Yield

Conditions & References und Destillieren des Reaktionsprodukts Baker; ; vol. 2; (1930); p. 117; Chem. Zentralbl.; vol. 101; nb. II; (1930); p. 3537 View in Reaxys

O

Br

O

OH

O

OH

O

O

Br

O

O

Rx-ID: 170830 View in Reaxys 221/328 Yield

Conditions & References T= 25 °C Bassett; Taylor; Journal of the Chemical Society; (1929); p. 1575 View in Reaxys

O

Br

Br

Br

O

Rx-ID: 174148 View in Reaxys 222/328 Yield

Conditions & References T= 180 °C , im Rohr Lyden; ; vol. 38; (1929); p. 19; Chem. Zentralbl.; vol. 101; nb. I; (1930); p. 2379 View in Reaxys

O

Br

O

HO

O

O

O

OH

O

O

Br

Rx-ID: 780290 View in Reaxys 223/328 Yield

Conditions & References T= 25 °C Bassett; Taylor; Journal of the Chemical Society; (1929); p. 1575 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Cl I

Al

Br

Br

Cl

Br

Cl

Rx-ID: 5801637 View in Reaxys 224/328 Yield

Conditions & References Dougherty; Journal of the American Chemical Society; vol. 51; (1929); p. 579 View in Reaxys

O

Br

Br

OH

Br

acid

Br

O Br

Br

Rx-ID: 6953603 View in Reaxys 225/328 Yield

Conditions & References Dworzak; Prodinger; Monatshefte fuer Chemie; vol. 53/54; (1929); p. 590 View in Reaxys

O

phosphorus trichloride-dibromide

O

Br

Br

Br

O

O

Br

Rx-ID: 6957682 View in Reaxys 226/328 Yield

Conditions & References Kirrmann; Annales de Chimie (Cachan, France); vol. <10>11; (1929); p. 232,271; Bulletin de la Societe Chimique de France; vol. <4>41; (1927); p. 319,320 View in Reaxys

Br Br

6.7-benzo-phthalide O

O

Rx-ID: 8257796 View in Reaxys 227/328 Yield

Conditions & References Mayer; Schaefer; Rosenbach; Archiv der Pharmazie (Weinheim, Germany); (1929); p. 578 View in Reaxys Br

Br

Br

Se

Se Br

Rx-ID: 457292 View in Reaxys 228/328 Yield

Conditions & References T= 130 °C Edwards et al.; Journal of the Chemical Society; (1928); p. 2300 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

S+

HO

Br–

Br

OH

S

HO

OH

Rx-ID: 746385 View in Reaxys 229/328 Yield

Conditions & References T= 80 °C , Geschwindigkeit Corran; Transactions of the Faraday Society; vol. 23; p. 605; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 1490 View in Reaxys T= 90 °C , Geschwindigkeit Corran; Transactions of the Faraday Society; vol. 23; p. 605; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 1490 View in Reaxys

Br

S+ Br–

S

HO

Rx-ID: 750221 View in Reaxys 230/328 Yield

Conditions & References T= 80 °C , Geschwindigkeit Corran; Transactions of the Faraday Society; vol. 23; p. 605; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 1490 View in Reaxys T= 90 °C , Geschwindigkeit Corran; Transactions of the Faraday Society; vol. 23; p. 605; Chem. Zentralbl.; vol. 99; nb. I; (1928); p. 1490 View in Reaxys

Cl Br

O

Br

Br

O

Br

O

Cl

Cl

Cl

Br

Cl

Br

Cl

Rx-ID: 6958984 View in Reaxys 231/328 Yield

Conditions & References Backer; Mook; Journal of the Chemical Society; (1928); p. 2127 View in Reaxys Mg+

Br–

Br

dry air Rx-ID: 7976733 View in Reaxys 232/328

Yield

Conditions & References Meisenheimer; Schlichenmaier; Chemische Berichte; vol. 61; (1928); p. 2043 View in Reaxys O

O S O

Br–

+Mg

O

Br

cyclohexanesulfonate magnesium Rx-ID: 8273522 View in Reaxys 233/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References Gilman; Heck; Journal of the American Chemical Society; vol. 50; (1928); p. 2228 View in Reaxys

O

Br

O

O

Br

O

O

O

Br

Rx-ID: 174147 View in Reaxys 234/328 Yield

Conditions & References T= 200 - 210 °C Lyden; ; vol. 35; p. 27; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 1813 View in Reaxys

Cl

Cl

Br Br

Br

Br

Cl Br

O Br

Cl

O

Rx-ID: 229183 View in Reaxys 235/328 Yield

Conditions & References beim Aufbewahren Smith; Journal of the Chemical Society; (1927); p. 1101 View in Reaxys T= 60 °C Smith; Journal of the Chemical Society; (1927); p. 1101 View in Reaxys

Cl

O

Cl Br

S+

N

Br–

S

O

Cl

Cl

Rx-ID: 663490 View in Reaxys 236/328 Yield

Conditions & References T= 20 - 60 °C , Geschwindigkeit Essex; Gelormini; Journal of the American Chemical Society; vol. 48; (1926); p. 889 View in Reaxys

O Br

O S O

Rx-ID: 737609 View in Reaxys 237/328 Yield

Conditions & References With water, potassium bromide Rodionow; Bulletin de la Societe Chimique de France; vol. <4> 39; (1926); p. 318; Bulletin de la Societe Chimique de France; vol. <4> 45; (1929); p. 119 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

O

Br

Br

H

Br

Br Br

Br

Rx-ID: 6950223 View in Reaxys 238/328 Yield

Conditions & References Lepingle; Bulletin de la Societe Chimique de France; vol. <4>39; (1926); p. 872 View in Reaxys

HO

H

H O

Br

H

O

Br

OH

both stereoisomer(ic)/s α-ethoxy-α-butylene Rx-ID: 7069978 View in Reaxys 239/328 Yield

Conditions & References T= 0 °C , nachfolgende Destillation des von Wasser und Bromwasserstoff befreiten Reaktionsgemisch mit absol.Alkohol Lepingle; Bulletin de la Societe Chimique de France; vol. <4>39; (1926); p. 872 View in Reaxys Br

O

O Br

p-pyromellitide O

O

Br

Rx-ID: 8285809 View in Reaxys 240/328 Yield

Conditions & References T= 163 - 163.5 °C de Diesbach; Zurbriggen; Helvetica Chimica Acta; vol. 8; (1925); p. 552 View in Reaxys

O O O

Br

Br

O

O Br

O

Rx-ID: 258159 View in Reaxys 241/328 Yield

Conditions & References bei der Destillation unter vermindertem Druck Ingold; Oliver; Thorpe; Journal of the Chemical Society; vol. 125; (1924); p. 2135 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Cl

Cl

Mg+

Br–

Cl

Br

C

Cl

Rx-ID: 61297 View in Reaxys 242/328 Yield

Conditions & References Binaghi; Gazzetta Chimica Italiana; vol. 53; (1923); p. 882 View in Reaxys N

N

Br

S

Br S

Rx-ID: 173200 View in Reaxys 243/328 Yield

Conditions & References T= 60 - 70 °C v.Braun; Engelbertz; Chemische Berichte; vol. 56; (1923); p. 1575 View in Reaxys T= 60 - 70 °C v.Braun; Engelbertz; Chemische Berichte; vol. 56; (1923); p. 1575 View in Reaxys O

O

Br

H OH

Br

O

O O

Rx-ID: 191091 View in Reaxys 244/328 Yield

Conditions & References Lachman; Journal of the American Chemical Society; vol. 45; (1923); p. 2359 View in Reaxys

Cl Br

O

Cl

Rx-ID: 227633 View in Reaxys 245/328 Yield

Conditions & References T= 25 °C , und Erwaermen unter Ausschluss von Feuchtigkeit Vanderstichele; Journal of the Chemical Society; vol. 123; (1923); p. 1228 View in Reaxys Crompton; Triffitt; Journal of the Chemical Society; vol. 119; (1921); p. 1874 View in Reaxys T= 25 °C , und Stehenlassen unter Ausschluss von Feuchtigkeit Vanderstichele; Journal of the Chemical Society; vol. 123; (1923); p. 1228 View in Reaxys Crompton; Triffitt; Journal of the Chemical Society; vol. 119; (1921); p. 1874 View in Reaxys

Cl O

Br

O

Cl

Cl

Br Br

Br

Cl

Rx-ID: 6958633 View in Reaxys 246/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References Vanderstichele; Journal of the Chemical Society; vol. 123; (1923); p. 1228 View in Reaxys Crompton; Triffitt; Journal of the Chemical Society; vol. 119; (1921); p. 1874 View in Reaxys McKie; Journal of the Chemical Society; vol. 123; (1923); p. 2215; Journal of the Chemical Society; vol. 125; (1924); p. 1077 View in Reaxys

O

Br O

α-bromo-α.α-hexamethylene-butyrolacetone-αcarboxylic acid ethyl ester

Br Br

O O

Rx-ID: 7976734 View in Reaxys 247/328 Yield

Conditions & References bei der Destillation unter vermindertem Druck Baker; Ingold; Journal of the Chemical Society; vol. 123; (1923); p. 125,130 View in Reaxys

Cl

Cl

Mg+

Br–

Br

C

Cl

Rx-ID: 211768 View in Reaxys 248/328 Yield

Conditions & References Binaghi; Gazzetta Chimica Italiana; vol. 52 II; (1922); p. 138 View in Reaxys

Br

Br Br

Br

Br

C

Mg Br

Br

Rx-ID: 211850 View in Reaxys 249/328 Yield

Conditions & References Produkt: Aethan, Acetylen Binaghi; Gazzetta Chimica Italiana; vol. 52 II; (1922); p. 136 View in Reaxys N

Br

Br

As

As

N

Rx-ID: 244725 View in Reaxys 250/328 Yield

Conditions & References T= 100 °C Steinkopf; Donat; Jaeger; Chemische Berichte; vol. 55; (1922); p. 2610 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

N Br As

Br N

Br

as-ethyl-pentamethylenarsine

Rx-ID: 5725753 View in Reaxys 251/328 Yield

Conditions & References T= 75 °C Steinkopf; Donat; Jaeger; Chemische Berichte; vol. 55; (1922); p. 2610 View in Reaxys N

As

Br

As

Br

Br

dipropylarsenic cyanide(?)

N

Rx-ID: 7074825 View in Reaxys 252/328 Yield

Conditions & References T= 100 - 150 °C Steinkopf; Donat; Jaeger; Chemische Berichte; vol. 55; (1922); p. 2610 View in Reaxys

I

I

Br

C

Mg Br

I

Rx-ID: 172377 View in Reaxys 253/328 Yield

Conditions & References Produkt: Aethyljodid, Methylenjodid Oddo; Binaghi; Gazzetta Chimica Italiana; vol. 51 II; (1921); p. 334 View in Reaxys

Br

Br

O

O

O

O

Br

Yield

cis-α-bromo-α.α-tetramethylene-butyrolactone-α-carboxylic acid ethyl ester

trans-α-bromo-α.α-tetramethylene-butyrolactone-α-carboxylic acid ethyl ester Rx-ID: 8288919 View in Reaxys 254/328

Conditions & References bei der Destillation Becker; Thorpe; Journal of the Chemical Society; vol. 117; (1920); p. 1582 Anm., 1585 View in Reaxys

Br

O

Hg2F2

Br

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

F

Br

O

O

O F

F

Rx-ID: 6919496 View in Reaxys 255/328 Yield

Conditions & References T= 160 - 200 °C Swarts; Bulletin de la Societe Chimique de France; vol. <4>25; (1919); p. 105; Journal de Chimie Physique et de Physico-Chimie Biologique; vol. 17; (1919); p. 32,70 View in Reaxys Mg+

Br

Br

Br

I–

Rx-ID: 7976732 View in Reaxys 256/328 Yield

Conditions & References Datta; Mitter; Journal of the American Chemical Society; vol. 41; (1919); p. 291 View in Reaxys O

O P

O

Br

Br

O

(C2H5O)2POCH2CO2C2H5

O

Rx-ID: 6726674 View in Reaxys 257/328 Yield

Conditions & References analog reagieren die Aethylester von halogenierten Propionsaeuren und Buttersaeuren Arbusow; Dunin; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 46; (1914); p. 297; Chem. Zentralbl.; vol. 85; nb.

I; (1914); p. 2156 View in Reaxys

O

OH

O

Br Br

Br

Br

H

O

Rx-ID: 7053809 View in Reaxys 258/328 Yield

Conditions & References Meyer,K.H.; Lenhardt; Justus Liebigs Annalen der Chemie; vol. 398; (1913); p. 68 View in Reaxys

HO

O

Br

N N

diluted mineral acid

N N

Rx-ID: 8260201 View in Reaxys 259/328 Yield

Conditions & References T= 100 °C , das Hydrobromid reagiert Charrier; Ferreri; Gazzetta Chimica Italiana; vol. 43 I; (1913); p. 557 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br As

Br Br

As

Br

Rx-ID: 460343 View in Reaxys 260/328 Yield

Conditions & References T= 85 °C Winmill; Journal of the Chemical Society; vol. 101; (1912); p. 719 View in Reaxys N Br

N

Br

N

N

Br

Rx-ID: 173304 View in Reaxys 261/328 Yield

Conditions & References v. Braun; Chemische Berichte; vol. 43; (1910); p. 3213 View in Reaxys

N N

Br

N

Br

Br

N-cyano-piperidine N

Rx-ID: 5739546 View in Reaxys 262/328 Yield

Conditions & References v. Braun; Chemische Berichte; vol. 42; (1909); p. 2052 View in Reaxys

OH N

N+

Br

Br

Br

O

Br

HO

Br

Br

benzene and bromobenzene

Br

Rx-ID: 6726280 View in Reaxys 263/328 Yield

Conditions & References beim Behandeln von Benzoldiazoniumperbromid 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

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

Br Br

Al

Br

O

H

Br

Rx-ID: 8213611 View in Reaxys 264/328 Yield

Conditions & References bei der trocknen Destillation Plotnikow; Chem. Zentralbl.; vol. 80; nb. I; (1909); p. 492 View in Reaxys O O

O

O

O

O

Br

Br

H

O

Br HO

O

OH O

O

Rx-ID: 7057726 View in Reaxys 265/328 Yield

Conditions & References Blaise; Gault; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 147; (1908); p. 200; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 148; (1909); p. 177 View in Reaxys

Br

N+

Br–

N-ethyl-piperidine

Rx-ID: 8282149 View in Reaxys 266/328 Yield

Conditions & References Schmelzen v. Braun; Chemische Berichte; vol. 41; (1908); p. 2160 View in Reaxys Br

Br

OH

O Br Br

O Br

O

O Br

Br

O

O

Br

Rx-ID: 189055 View in Reaxys 267/328 Yield

Conditions & References Freundler; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 140; (1905); p. 1693; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 143; (1906); p. 683 View in Reaxys Freundler; Bulletin de la Societe Chimique de France; vol. <4>1; (1907); p. 67 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

O

Br

Br H

HN

Cl

Br

Br

H

Br

H

NH

O

HO

Cl N H

O

H

O

O

Rx-ID: 7064189 View in Reaxys 268/328 Yield

Conditions & References T= 160 °C Diels; Ochs; Chemische Berichte; vol. 40; (1907); p. 4573 View in Reaxys H Br

-1

Br

OH

O

Br Br

Ta

H

Br (v5)

Br

-1 O Ta 5 2

Rx-ID: 26344489 View in Reaxys 269/328 Yield

Conditions & References Weinland, F. R.; Storz, L.; Zeitschrift fuer Anorganische und Allgemeine Chemie; vol. 54; (1907); p. 223 - 243 ; (from Gmelin) View in Reaxys vol. Ta: MVol.B1; 7, page 141 - 159 ; (from Gmelin) View in Reaxys

OH

Br

Br

Br

Br

Br O

Br

Br

Br

Rx-ID: 188481 View in Reaxys 270/328 Yield

Conditions & References T= 150 °C Ponzio; Gazzetta Chimica Italiana; vol. 36 II; (1906); p. 149; Chem. Zentralbl.; vol. 77; nb. I; (1906); p. 1691 View in Reaxys O

O

Br

O

Br

OH

H

HO

OH NH 2

NH 2

Rx-ID: 6936093 View in Reaxys 271/328 Yield

Conditions & References Leuchs; Geiger; Chemische Berichte; vol. 39; (1906); p. 2645 View in Reaxys

OH Br

Br

N

Br

Br

H

Rx-ID: 8213610 View in Reaxys 272/328 Yield

Conditions & References Hantzsch; Graf; Chemische Berichte; vol. 38; (1905); p. 2157 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O OH

Br Br

O

O

P

Br

trimethylparaconic acid ethyl ester

Br O

Rx-ID: 7088861 View in Reaxys 273/328 Yield

Conditions & References Noyes; Patterson; American Chemical Journal; vol. 28; (1902); p. 230 View in Reaxys

N N Br

2-phenyl-4-α-pyridyl-pyrimidone-(6)

N

O

Rx-ID: 5541834 View in Reaxys 274/328 Yield

Conditions & References T= 150 °C , Das Hydrobromid reagiert Pinner; Chemische Berichte; vol. 34; (1901); p. 4247 View in Reaxys

N

N

Br

N Br

triethylphenylammonium bromide

N

Rx-ID: 6220729 View in Reaxys 275/328 Yield

Conditions & References T= 100 °C Scholl; Noerr; Chemische Berichte; vol. 33; (1900); p. 1555 View in Reaxys v.Braun; Chemische Berichte; vol. 33; (1900); p. 1448 View in Reaxys

Br N

hydroxylamine hydrochloride

Br

NH 2

Br

Br Br

Rx-ID: 7060998 View in Reaxys 276/328 Yield

Conditions & References Kuehner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 31; (1899); p. 1045; Chem. Zentralbl.; vol. 71; nb. I; (1900); p. 958 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

O

HO

Br

Br

bromine (2 atomic weight)

Br

H O

Rx-ID: 5854071 View in Reaxys 277/328 Yield

Conditions & References T= 150 °C Epstein; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 124; (1897); p. 689 View in Reaxys Crafts; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 56; (1863); p. 707; Justus Liebigs Annalen der Chemie; vol. 129; (1864); p. 50 View in Reaxys Br Br

O

O

O

α-methyl-butyrolactonecarboxylic acid ethyl ester

O

Rx-ID: 6800402 View in Reaxys 278/328 Yield

Conditions & References T= 260 °C Marburg; Justus Liebigs Annalen der Chemie; vol. 294; (1897); p. 125 Anm. View in Reaxys Br

O

O

O

barytes

O

Br

α-methyl-butyrolactonecarboxylic acid ethyl ester Rx-ID: 6800403 View in Reaxys 279/328 Yield

Conditions & References Marburg; Justus Liebigs Annalen der Chemie; vol. 294; (1897); p. 125 Anm. View in Reaxys

Br

O

Br

Br O

Br Br

HO Br

Br

H

α.α-dibromo-propionic acid ethyl ester

O

Rx-ID: 7053863 View in Reaxys 280/328 Yield

Conditions & References T= 180 - 200 °C Epstein; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 124; (1897); p. 689 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

N N Br

Br

H

3-isopropyl-4-cyano-isocarbostyril

O

Rx-ID: 8249417 View in Reaxys 281/328 Yield

Conditions & References Lehmkuhl; Chemische Berichte; vol. 30; (1897); p. 896 View in Reaxys

O

N

Br N

Br O

Rx-ID: 416359 View in Reaxys 282/328 Yield

Conditions & References in der Hitze Lengfeld; Stieglitz; American Chemical Journal; vol. 17; (1895); p. 100 View in Reaxys

O

H N

Cl

N

Br

Br O

H

Cl

O

Rx-ID: 7448512 View in Reaxys 283/328 Yield

Conditions & References Lengfeld; Stieglitz; American Chemical Journal; vol. 17; (1895); p. 100 View in Reaxys

O

N

Br

H

Cl

H N

Br

H N

Cl

Cl

Br

O

O

Rx-ID: 7448514 View in Reaxys 284/328 Yield

Conditions & References Lengfeld; Stieglitz; American Chemical Journal; vol. 17; (1895); p. 100 View in Reaxys

O

Cl

N

H Br

H N

Br Br

H N

Cl

Cl

O

O

Rx-ID: 8262437 View in Reaxys 285/328

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Yield

Conditions & References Lengfeld; Stieglitz; American Chemical Journal; vol. 17; (1895); p. 100 View in Reaxys

3 OH

Br

Br

H

CaO

Br2Ca

Rx-ID: 26454474 View in Reaxys 286/328 Yield

Conditions & References in neat (no solvent), at heating decomposition under formation of CaO, HBr and C2H5Br; Roques, F.; J. Pharm. (6); vol. 1; (1895); p. 301 - 303 ; (from Gmelin) View in Reaxys in neat (no solvent), at heating decomposition under formation of CaO, HBr and C2H5Br; vol. Ca: MVol.B2; 148, page 602 - 605 ; (from Gmelin) View in Reaxys O

O

O Br

Br

Br

O

O Br O

Rx-ID: 245826 View in Reaxys 287/328 Yield

Conditions & References Erhitzen unter vermindertem Druck Epprecht; Justus Liebigs Annalen der Chemie; vol. 278; (1894); p. 79 View in Reaxys

Br

Br Br

Br

O

O

sulfur Br

Rx-ID: 6954774 View in Reaxys 288/328 Yield

Conditions & References Genvresse; Bulletin de la Societe Chimique de France; vol. <3>11; (1894); p. 890 View in Reaxys

Cl

Br Br

Br

Br

iron

Br

Rx-ID: 7060994 View in Reaxys 289/328 Yield

Conditions & References T= 100 °C Meyer,V.; Petrenko-Kritschenko; Chemische Berichte; vol. 25; (1892); p. 3307 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

O

O

Br Br

Br

O

O

O

O

Rx-ID: 8263351 View in Reaxys 290/328 Yield

Conditions & References T= 120 °C , im geschlossenen Rohr Bruehl; Chemische Berichte; vol. 24; (1891); p. 3410 View in Reaxys H

O Br

Br

P

Br

metaphosphoric acid

O

O

Rx-ID: 6215733 View in Reaxys 291/328 Yield

Conditions & References Thorpe; North; Journal of the Chemical Society; vol. 57; (1890); p. 634 View in Reaxys

Br

Br

O

Br

H

Rx-ID: 6682579 View in Reaxys 292/328 Yield

Conditions & References Kischner; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 22; (1890); p. 29 View in Reaxys O

O

O–

Br

Na +

alcohol. solution

O Cl Br

NaBr

ethyl bromoacetate

p-dioxy-terephthalic acid diethyl ester Rx-ID: 7084300 View in Reaxys 293/328

Yield

Conditions & References T= 100 °C , unter Druck Mewes; Justus Liebigs Annalen der Chemie; vol. 245; (1888); p. 59 View in Reaxys Br

Br Si

OH

Br

Br

Br H N 2

N

S

S

8

silicic acid

NH 2

Rx-ID: 8287004 View in Reaxys 294/328 Yield

Conditions & References Reynolds; Journal of the Chemical Society; vol. 53; (1888); p. 861; Journal of the Chemical Society; vol. 61; (1892); p. 251 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

O O

O

Br Br

Br

O

O

O O

Rx-ID: 6207658 View in Reaxys 295/328 Yield

Conditions & References Ladenburg; Wichelhaus; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 165 View in Reaxys Arnhold; Justus Liebigs Annalen der Chemie; vol. 240; (1887); p. 199 View in Reaxys

Br

Bi

Bi Br

Rx-ID: 26519183 View in Reaxys 296/328 Yield

Conditions & References With Br2 in petroleum ether, cooling Marquardt, A.; Ber. Dtsch. Chem. Ges.; vol. 20; (1887); p. 1516 - 1523 View in Reaxys vol. Bi: Org.Verb.; 1.3.3.1.1, page 46 - 55 ; (from Gmelin) View in Reaxys H

OH N

HO

O

OH

O

Br

Br

Br

H

N

H 2N 2

H

O

H

NH 2

Rx-ID: 7063149 View in Reaxys 297/328 Yield

Conditions & References Mulder; Recueil des Travaux Chimiques des Pays-Bas; vol. 5; (1886); p. 65 View in Reaxys

O

O

O

OH

Br

halogen hydrogen Rx-ID: 5853378 View in Reaxys 298/328 Yield

Conditions & References Sapper; Justus Liebigs Annalen der Chemie; vol. 211; (1882); p. 178 View in Reaxys

O Br

zinc

O Br

zinc bromide

carbon monoxide

propionic acid ethyl ester and symm.dimethylsuccinic acid (?)

Rx-ID: 7089313 View in Reaxys 299/328

Yield

Conditions & References Scherks; Monatshefte fuer Chemie; vol. 2; (1881); p. 546 View in Reaxys

H

H O

Br– N+

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

N

Br

N H

Rx-ID: 8258019 View in Reaxys 300/328 Yield

Conditions & References bei der Destillation; Produkt 5:Aethylen Reboul; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 92; (1881); p. 1464; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1881); p. 408 View in Reaxys O O

Br

O Br

O

Br

O

HO OH

O O

O

O

Rx-ID: 5805223 View in Reaxys 301/328 Yield

Conditions & References T= 100 °C , Verb. 1: 1 Mol.-Gew. Urech; Chemische Berichte; vol. 13; (1880); p. 1692; Chemische Berichte; vol. 14; (1881); p. 340 View in Reaxys

O

O

bromine (4 atomic weight) Br

O

Br

OH

Br

dibromoacetic acid tribromoethyl ester Rx-ID: 6212742 View in Reaxys 302/328 Yield

Conditions & References T= 160 °C Steiner; Chemische Berichte; vol. 7; (1874); p. 506 View in Reaxys Carius; Chemische Berichte; vol. 3; (1870); p. 336 View in Reaxys Urech; Chemische Berichte; vol. 13; (1880); p. 1692; Chemische Berichte; vol. 14; (1881); p. 340 View in Reaxys Br O

silver O O

Br

OH

symm.diethylsuccinic acid diethyl ester and isocrotonic acid ester

O

Rx-ID: 6731554 View in Reaxys 303/328 Yield

Conditions & References Hell; Muehlhaeuser; Chemische Berichte; vol. 13; (1880); p. 474,479 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O Br

Br

H

N

ethyl-o-phenetidine

Rx-ID: 8276152 View in Reaxys 304/328 Yield

Conditions & References bei der trocknen Destillation Foerster; Journal fuer Praktische Chemie (Leipzig); vol. <2>21; (1880); p. 346 View in Reaxys

O

OH

Br

Br O

O

O

O

Br

Br

O O

Rx-ID: 188831 View in Reaxys 305/328 Yield

Conditions & References Kessel; Chemische Berichte; vol. 11; (1878); p. 1916 View in Reaxys Br OH

Br

O

Br O

Br

Br

Br

O Br

dibromoacetic acid ester O

Rx-ID: 7073740 View in Reaxys 306/328 Yield

Conditions & References Kessel; Chemische Berichte; vol. 11; (1878); p. 1916 View in Reaxys

Cl

O Br

P

Br

Br

POCl2Br

Cl

Rx-ID: 7084944 View in Reaxys 307/328 Yield

Conditions & References Geuther; Hergt; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1876); p.

206 View in Reaxys

Cl

O P Cl

Br Br

Br

PBr Br Br

O Cl

P ClBr

Br P

Br

Br

Rx-ID: 26453390 View in Reaxys 308/328 Yield

Conditions & References in neat (no solvent), reaction at 60°C; Geuther, A.; Hergt, O.; Jenaische Z. Naturwiss. (2. Suppl.-H.); vol. 10; (1876); p. 104 - 106 ; (from Gmelin) View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

in neat (no solvent), reaction at 60°C; vol. P: MVol.C; 225, page 516 - 517 ; (from Gmelin) View in Reaxys

Br

O

α-acrylcolloid

Br O

Rx-ID: 6395484 View in Reaxys 309/328 Yield

Conditions & References Wagner; Tollens; Justus Liebigs Annalen der Chemie; vol. 171; (1874); p. 341 View in Reaxys

O

O

HO

Br

Br

Br

Br

Br

H O

Rx-ID: 8255172 View in Reaxys 310/328 Yield

Conditions & References T= 140 - 150 °C Schuetzenberger; Chemische Berichte; vol. 6; (1873); p. 71 View in Reaxys Crafts; Justus Liebigs Annalen der Chemie; vol. 129; (1864); p. 50 View in Reaxys

O

O

H

Br Br

Br

Br

H O

Br

Rx-ID: 7443667 View in Reaxys 311/328 Yield

Conditions & References Paterno; Chemische Berichte; vol. 5; (1872); p. 288 View in Reaxys Cl

Br O

OH

OH

Br

HO

Cl

Cl

OH

Br H

O

O

Rx-ID: 188955 View in Reaxys 312/328 Yield

Conditions & References T= 160 °C Carius; Justus Liebigs Annalen der Chemie; vol. 155; (1870); p. 35 View in Reaxys O

Br

O

Br

HO

OH

Br Br

Br

H 2N 2

O O

Br

O

Rx-ID: 6682191 View in Reaxys 313/328 Yield

Conditions & References Ladenburg; Wichelhaus; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 165 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Br

Br

O

O

Br

O

Br

O

Br

O Br

O

O

O

Rx-ID: 7066416 View in Reaxys 314/328 Yield

Conditions & References Ladenburg; Wichelhaus; Justus Liebigs Annalen der Chemie; vol. 152; (1869); p. 165 View in Reaxys SH

Br

Br

Br

Br

H

BrS Rx-ID: 6210724 View in Reaxys 315/328

Yield

Conditions & References Friedel; Ladenburg; Justus Liebigs Annalen der Chemie; vol. 145; (1868); p. 189 View in Reaxys Br

O

Br

Cl

P

Br

Br

Cl

Rx-ID: 6800400 View in Reaxys 316/328 Yield

Conditions & References Lieben; Justus Liebigs Annalen der Chemie; vol. 146; (1868); p. 225 View in Reaxys

O

Br

Br

Br

Cl

P

Br

chlorobromobutane

Br

Br

Rx-ID: 7071514 View in Reaxys 317/328 Yield

Conditions & References Lieben; Justus Liebigs Annalen der Chemie; vol. 146; (1868); p. 225 View in Reaxys Br

O

Br

Br

Cl

P

Br

chlorobromopropane

Br

Br

Rx-ID: 7071516 View in Reaxys 318/328 Yield

Conditions & References Lieben; Justus Liebigs Annalen der Chemie; vol. 146; (1868); p. 225 View in Reaxys

O

Br

O O

O

Br

OH

HO Br

H O

O

Rx-ID: 7059134 View in Reaxys 319/328 Yield

Conditions & References T= 100 °C Gal; Justus Liebigs Annalen der Chemie; vol. 142; (1867); p. 371 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

Cl

O

Br

P

O

Br Br Cl

Cl

P ClBr

Rx-ID: 26368655 View in Reaxys 320/328 Yield

Conditions & References in neat (no solvent), dropping Br2 into POCl2C2H5;; separating via fractionation; Menschutkin, N.; Liebigs Annalen der Chemie; vol. 139; (1866); p. 343 - 354 ; (from Gmelin) View in Reaxys in neat (no solvent), dropping Br2 into POCl2C2H5;; separating via fractionation; vol. P: MVol.C; 225, page 516 - 517 ; (from Gmelin) View in Reaxys Br

I

Br

Br

Rx-ID: 5801636 View in Reaxys 321/328 Yield

Conditions & References Friedel; Justus Liebigs Annalen der Chemie; vol. 135; (1865); p. 206 View in Reaxys

Br

Br

(v2)

Br

Zn

Br

Rx-ID: 211851 View in Reaxys 322/328 Yield

Conditions & References Alexejew; Beilstein; Bulletin de la Societe Chimique de France; vol. <2>2; (1864); p. 52; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1864); p. 470 View in Reaxys Br

Br

H

Rx-ID: 6800396 View in Reaxys 323/328 Yield

Conditions & References T= 100 °C Berthelot; Justus Liebigs Annalen der Chemie; vol. 104; (1857); p. 184 View in Reaxys Berthelot; Justus Liebigs Annalen der Chemie; vol. 115; (1860); p. 114 View in Reaxys

(v2)

Br

Hg

Br

ethylmercury bromide

Br

Rx-ID: 8276143 View in Reaxys 324/328 Yield

Conditions & References Buckton; Justus Liebigs Annalen der Chemie; vol. 112; (1859); p. 221; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1859); p. 408 View in Reaxys

(v2)

Br

Br

Br

Zn

zinc bromide

O

Rx-ID: 8290527 View in Reaxys 325/328 Yield

Conditions & References Frankland; Justus Liebigs Annalen der Chemie; vol. 95; (1855); p. 49,51 View in Reaxys

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Bromoethane (Ethyl bromide; EtBr) [C2H5Br]

O

Br

Br

O Br

Br

O

Rx-ID: 178701 View in Reaxys 326/328 Yield

Conditions & References With ethanol Patent; Imbert; Konsortium f. elektroch. Ind.; DE212592 View in Reaxys

O O

O

O

Br

O

Br O Br

Rx-ID: 235519 View in Reaxys 327/328 Yield

Conditions & References T= 200 °C , Prod.5:Bromessigsaeure-aethylester, Prod.6:Dibromessigsaeure-aethylester; unter Druck McElvain; Anthes; Shapiro; Journal of the American Chemical Society; vol. 64; p. 2527,2531 View in Reaxys Br

<1-14C>-ethanol

aqueous hydrobromic acid Rx-ID: 6395478 View in Reaxys 328/328

Yield

Conditions & References With ethanol, sulfuric acid, Am C-Atom 1 mit Kohlenstoff-14 markiertes Bromaethan ist erhalten worden Wolff; Pichah; View in Reaxys

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