Azobisisobutyronitrile → Methyl 5-bromo-2-(bromomethyl)benzoate

Participants

Reaction Steps

The mixture of 3- and 5-bromo-2-methylbenzoic acid methyl ester (35.79 g; 156 mmol) is dissolved in carbon tetrachloride (200 mL). To the solution is added N-bromosuccinimide (29.5 g; 166 mmol), followed by AIBN (54 mg) and the mixture was heated at reflux temperature for 20 hours. Then the mixture was cooled to room temperature and the succinimide was filtered from solution and rinsed with carbon tetrachloride. The solvent was evaporated to yield a mixture of the title compound and 3-bromo-2-bromomethylbenzoic acid methyl ester (48.1 g; crude mass).

Provenance & Evidence