Benzophenone, 4-chloro-4'-methyl- → 4-(4-Chlorobenzoyl)benzyl bromide

Participants

Reaction Steps

A mixture of 4-(4-chlorobenzoyl)toluene (5.48 g, 23.8 mmol), dibenzoylperoxide (100 mg, 0.413 mmol), and N-bromosuccinimide (4.56 g, 25.6 mmol) in carbon tetrachloride (70 ml) was refluxed for 2 hours, cooled, filtered, and evaporated under vacuum. The residue was chromatographed on silica gel (1 kg) eluted with 97:3 (v/v) hexane-ethyl acetate using a preparative high-performance liquid chromatograph. Appropriate fractions were pooled and evaporated under vacuum to provide 4.61 g (63%) of 4-(4-chlorobenzoyl)benzyl bromide, m.p. 103°-104° C.

Provenance & Evidence