Azobisisobutyronitrile → 3-(Bromomethyl)-4-nitrobenzoic acid

Participants

Reaction Steps

A solution of 3-methyl-4-nitrobenzoic acid (539 mg, 2.98 mmol) in benzene (20 mL) was heated to reflux in a sealed tube after which N-bromosuccinimide (679 mg, 3.43 mol) and AIBN (49 mg, 0.298 mol) were carefully added in a portion wise manner over 5 min. After 12 h the mixture was cooled to room temperature, and the succinimide was filtered off and washed with benzene (5 mL×3). The solvent was removed under reduced pressure and purified by column chromatography to give the desired product 3-(bromomethyl)-4-nitrobenzoic acid (553 mg, 68% yield) as a viscous yellow oil.

Provenance & Evidence