2-bromo-1-(bromomethyl)-4-nitrobenzene synthesis
- Product Name:2-bromo-1-(bromomethyl)-4-nitrobenzene
- CAS Number:940-05-6
- Molecular formula:C7H5Br2NO2
- Molecular Weight:294.93
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Yield: 33%
Reaction Conditions:
with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane at 70; for 3 h;
Steps:
75 2-Bromo-1-(bromomethyl)-4-nitrobenzene
To a mixture of 2-bromo-6-nitrobenzene (1.08g, 5.00 mmol) and N-bromosuccinimide (908mg, 5.10 mmol), α,α'-azobisisobutyronitrile (AIBN) (28mg) was added in carbon tetrachloride (15mL) at 70°C and stirred at 70°C for 3 hours. Further, AIBN (82mg) was added portionwise with stirring 70°C for 4 hours. After a dilution with chloroform, precipitate was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1) to give 2-bromo-1-(bromomethyl)-4-nitrobenzene (493mg, 33%). 1H-NMR (CDCl3) δ: 4.62(2H,s), 7.65(1H,d,J=8.4Hz), 8.17(1H,dd,J=8.4, 2.2Hz), 8.46(1H,d,J=2.2Hz)
References:
Dainippon Sumitomo Pharma Co., Ltd. EP1844768, 2007, A1 Location in patent:Page/Page column 39
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