Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

Participants

Reaction Steps

A solution of 4-bromophenol (17.3 g) in dimethylformamide (200 mL) was treated with potassium carbonate (15.2 g) followed by benzyl bromide (17.1 g 11.9 mL). After stirring for 16 hours at ambient temperature, the reaction mixture was diluted with water and hexane. The aqueous layer was extracted with hexane:ether (5:1). The organic extracts were washed (water, 1N sodium hydroxide, brine), dried and evaporated to give the bromobenzene as a white solid (23.4 g); NMR (CDCl3): 5.03 (s, 2), 6.85 (dd, 2, J1 =5, J2 =2), 7.3-7.4 (m, 7); MS: m/z=263(M+1). This material was used in the next step without further purification.

Provenance & Evidence