Water → 1-(Benzyloxy)-2-bromobenzene

Participants

Reaction Steps

A solution of 2-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 3 hours at the room temperature, the reaction mixture was diluted water and hexane. The aqueous layer was extracted with hexane; and the organic layers were washed (water, 1N sodium hydroxide, brine), dried and evaporated to give the product as a colorless oil (22.94 g). This material was fractionally distilled under reduced pressure to afford the bromobenzene (16.52 g); bp 110°-145° C. (1333 Pa); NMR (CDCl3): 5.17 (s, 2), 6.65 (d of t,1, J=8, J=1), 6.92-6.96 (d of d, 1, J=8, J=1), 7.19-7.26 (m, 1), 7.33-7.42 (m, 3), 7.46-7.50 (m, 2), 7.55 (d of d, 1, J=9, J=2). This material was used in the next step without further purification.

Provenance & Evidence