Benzoyl Peroxide → 4-(Bromomethyl)-3-chlorobenzonitrile

Participants

Reaction Steps

A mixture of 3-chloro-4-methylbenzonitrile (4.8 g), N-bromosuccinimide (5.5 g), dibenzoyl peroxide (0.43 g) and carbon tetrachloride (30 mL) was heated a reflux for 2 hours. The mixture was cooled to room temperature, filtered and washed with dichloromethane. The filtrated was washed with water, dried over sodium sulfate and the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 19:1 by volume) gave title compound, 4.1 g.

Provenance & Evidence