m-Tolylacetic acid → 2-(3-(Bromomethyl)phenyl)acetic acid

Participants

Reaction Steps

To a solution of m-tolylacetic acid (25.00 g, 166.5 mmol) in anhydrous carbon tetrachloride (200 ml) was added N-bromosuccinimide (30.00 g, 168.6 mmol), and the mixture was gradually heated to the boiling point. After heating the mixture under reflux for 5.5 hr, the reaction mixture was cooled to room temperature, the insoluble material was removed by filtration and washed twice with carbon tetrachloride (100 ml). The filtrate was concentrated, carbon tetrachloride (60 ml) was added and the residue was dissolved by heating at about 70° C. The solution was cooled to about 40° C., and hexane (300 ml) was added dropwise. After stirring at room temperature for 30 min, the precipitated crystals were filtered, washed with hexane and dried under reduced pressure to give (3-bromomethylphenyl)acetic acid (22.80 g, 99.53 mmol, yield 59.8%) as a white solid.

Provenance & Evidence