2-Bromo-1-(bromomethyl)-4-fluorobenzene

1422-53-3

61150-57-0

General procedure for the synthesis of 2-bromo-4-fluorobenzyl bromide from 2-bromo-4-fluorotoluene: In a round-bottomed flask equipped with a reflux condenser, 2-bromo-4-fluorotoluene (15 g, 79.3 mmol), N-bromosuccinimide (18.08 g, 101.6 mmol) and 2,2'-azobisisobutyronitrile (3.9 g, 23.8 mmol) were dissolved in carbon tetrachloride (150 mL). The reaction mixture was heated to reflux for 21 hours. After completion of the reaction, the mixture was cooled and the solvent was removed by distillation under reduced pressure. The crude product was suspended in dichloromethane and the organic layer was washed with water. Subsequently, the organic layer was washed with saturated aqueous sodium chloride solution and dried with anhydrous sodium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain the crude product. Purification of the crude product by column chromatography (eluent: 1% hexane solution of ethyl acetate tapered to 10% hexane solution of ethyl acetate) afforded 2-bromo-4-fluorobenzyl bromide as an oily white solid (18.5 g, 87% yield).GC-MS analysis showed m/z 268 [M]+.