N-bromobutanimide → 3-(Bromomethyl)-4-chlorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

(Step 1) To a solution of 4-chloro-3-methylbenzonitrile (1 g) in t-butylacetic acid (10 ml) were added N-bromosuccinimide (1.5 g) and azobisisobutyronitrile (0.05 g), and the mixture was stirred at 90° C. for 12 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:1-1:9) to give 3-(bromomethyl)-4-chlorobenzonitrile (1.5 g) as a white solid.

Provenance & Evidence