Phosphorus tribromide → 2-(Bromomethyl)-1-chloro-3-[(phenylmethyl)oxy]benzene

Participants

Reaction Steps

To a solution of {2-chloro-6-[(phenylmethyl)oxy]phenyl}methanol (for a preparation see Intermediate 7) (1.1 g, 4.42 mmol) in DCM (12 ml) at 0-5° C. under nitrogen was added dropwise a solution of phosphorus tribromide (0.417 ml, 4.42 mmol, Aldrich) in DCM (3 ml). The solution was allowed to warm to ambient temperature and stirred for 3 h. The solution in an ice-water bath was diluted with dichloromethane (40 ml) and then treated with saturated aqueous sodium hydrogen carbonate (20 ml). The phases were separated and the organic extract dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound as a yellow oil (0.829 g); LCMS: (System 1) (M-H)−=311, tRET=3.84 min.

Provenance & Evidence