Benzoyl Peroxide → 2-(Bromomethyl)-7-chloroquinoline

Participants

Reaction Steps

A stirred suspension of 7-chloroquinaldine (18.0 g, 0.10 mol), N-bromosuccinimide (18.0 g, 0.10 mol), and benzoyl peroxide (1.0 g, 0.004 mol) in CCl4 (400 mL) is illuminated with a 300 W reflector bulb for 6 hours. The reaction mixture is cooled and filtered through a plug of silica using hexane:ethyl acetate (7:3). The yellow filtrate is concentrated to give a crude mixture of unreacted starting material together with the monobromo and less polar dibromo products. The crude material is purified by flash chromatography (preabsorbed on silica Merck 60 with methylene chloride and then eluted with hexane:ethyl acetate 95:5), to yield fairly pure title product as an off-white solid. (17.31 g, 48.9% yield based on recovered starting material, m.p. 111°-112° C.).

Provenance & Evidence