Benzoyl Peroxide → 3-(bromomethyl)phenyl benzoate

Participants

Reaction Steps

To a solution of 20.83 g (0.098 mol) of 3-methylphenyl benzoate in 280 mL of carbon tetrachloride was added a catalytic amount of benzoyl peroxide, followed by 20.96 g (0.118 mol) of N-bromosuccinimide. The reaction mixture was stirred and heated under reflux overnight. After cooling to room temperature, the solid material was filtered off. The filtrate was washed with 100 mL of water. The organic phase was removed and dried over magnesium sulfate, filtered and evaporated to dryness in a rotary evaporator. The crude product (31.3 g) was purified by HPLC to give 20.61 g and was used directly in the next step.

Provenance & Evidence