Methyl o-toluate → Methyl 2-(bromomethyl)benzoate

Participants

Reaction Steps

A mixture of 2-methyl-benzoic acid methyl ester (1.53 g, 10 mmol), N-bromosuccinamide (1.95 g, 11 mmol), and benzoyl peroxide (0.056 g, 0.21 mmol) in carbon tetrachloride (20 mL) was heated at reflux until the starting materials were mostly consumed. Workup and silica gel column chromatography using 5% ethyl acetate in hexane afforded 2-bromomethyl-benzoic acid methyl ester (2.0 g, 87%). GC-MS: m/z 230 (M1)+.

Provenance & Evidence