Benzyl Bromide → {2-Chloro-6-[(phenylmethyl)oxy]phenyl}methanol

Participants

Reaction Steps

To a solution of 3-chloro-2-(hydroxymethyl)phenol (for a preparation see Intermediate 6)(1.37 g, 8.62 mmol) in absolute ethanol (30 ml) was added 2 M sodium hydroxide (4.74 ml, 9.49 mmol) and then benzyl bromide (1.03 ml, 8.62 mmol, Aldrich). The solution was stirred at ambient temperature for 3 days under nitrogen. The solvent was removed under reduced pressure to leave an aqueous suspension. The aqueous residue was partitioned between 2 M aqueous sodium hydroxide (40 ml) and ethyl acetate (60 ml). The phases were separated and the aqueous phase extracted with ethyl acetate (40 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give the title compound as a very pale brown oil (1.87 g); LCMS: (System 1) (M-H)−=247, tRET=3.20 min.

Provenance & Evidence