N-bromobutanimide → HCID 13649657, compound

Participants

Reaction Steps

A refluxing mixture of 4-(2,6-dichlorobenzoyl)toluene (12.0 g, 45.2 mmol) and dibenzoylperoxide (90 mg, 0.37 mmol) in benzene (450 ml) was treated in portions with N-bromosuccinimide (8.83 g, 49.6 mmol), refluxed 1.5 hours, cooled, and evaporated to dryness under vacuum. The residue was triturated with diethyl ether (300 ml), filtered, and the filtrate was evaporated to dryness under vacuum. The crude product was chromatographed on a column of silica gel (700 g) eluted with 97:3 (v/v) hexaneethyl acetate to provide 7.49 g (48%) 4-(2,6-dichlorobenzoyl)benzyl bromide, m.p. 126°-130° C.

Provenance & Evidence