Phosphorus tribromide → 4-(Bromomethyl)-3-(trifluoromethyl)phenyl phenylmethyl ether

Participants

Reaction Steps

To a solution of [4-[(phenylmethyl)oxy]-2-(trifluoromethyl)phenyl]methanol (for a preparation see Intermediate 18)(3.11 g, 11.02 mmol) in DCM (40 ml) under nitrogen in an ice-water bath was added a solution of phosphorus tribromide (1.09 ml, 11.6 mmol, Aldrich) in DCM (20 ml). The solution was allowed to warm to ambient temperature and stirred for 1.5 h. The reaction mixture was poured onto ice-water (150 ml) and saturated aqueous sodium hydrogen carbonate (75 ml). The mixture was diluted with dichloromethane (100 ml), and the phases separated. The aqueous extract was washed with dichloromethane (50 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give 4-(bromomethyl)-3-(trifluoromethyl)phenyl phenylmethyl ether as a white solid (2.96 g).

Provenance & Evidence