Benzoyl Peroxide → Methyl 3-bromo-2-(bromomethyl)benzoate

Participants

Reaction Steps

A suspension of methyl 3-bromo-2-methylbenzoate (26.6 mmol), benzoyl peroxide (2.7 mmol) and NBS (32 mmol) in benzene (80 mL) was allowed to stir at reflux for 5 hr. The reaction mixture was filtered and the solid was washed with diethyl ether. The organic solutions were combined and washed with 10% Na2S2O3 and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give methyl 3-bromo-2-(bromomethyl)benzoate (26.6 mmol, 100%) as an oil.

Provenance & Evidence