N-bromobutanimide → 3-Bromomethyl-4-chloro-5-methyl-benzonitrile

Participants

Reaction Steps

A mixture of 4-chloro-3,5-dimethyl-benzonitrile (1.011 g, 6.10 mmol), N-bromosuccinimide (1.087 g, 6.10 mmol) and benzoyl peroxide (0.074 g, 0.305 mmol) in carbon tetrachloride (30 mL) was heated to reflux for 4 hr. The reaction mixture was cooled to room temperature and filtered. The filtrate was purified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexane) to give 3-bromomethyl-4-chloro-5-methyl-benzonitrile as an impure white solid (0.9938 g, 66%), which was used in the next step without further purification.

Provenance & Evidence