8-Methylquinoline → 8-(Bromomethyl)quinoline

Participants

Reaction Steps

A mixture of 8-methylquinoline (45 g, 0.314 mol), N-bromosuccinimide (55 g, 0.309 mol) and benzoyl peroxide (1.5 g) in carbon tetrachloride (250 mL) was refluxed for 7 hours. The reaction was filtered and evaporated, and the crude product was crystallized from methanol (70 mL) to give 37.7 g of product. The mother liquors were chromatographed on silica gel in chloroform to give 17 g of material which was crystallized from ethyl acetate:hexane to give an additional 12.0 g of product.

Provenance & Evidence