Bromine → 2-Bromo-1-[1-(2-naphthyl)cyclobutyl]ethanone

Participants

Reaction Steps

A solution of bromine (4.3 ml) in chloroform (20 ml) was added dropwise over 30 minutes at 10°-15° C. to a stirred solution of 1-[1-(2-naphthyl)cyclobutyl]-ethanone (20 g) in a mixture of methanol (20 ml) and chloroform (30 ml). The mixture was then stirred at ambient temperature for 1.5 hours, poured onto ice-water (300 ml) and the product extracted into dichloromethane (3×150 ml). The extracts were washed with saturated aqueous sodium hydrogen carbonate solution, then water, dried over calcium chloride and the solvent removed in vacuo to give 2-bromo-1-[1-(2-naphthyl)cyclobutyl]-ethanone as an oil (24.0 g).

Provenance & Evidence