Hydrochloric Acid → 2-(Benzyloxy)-5-bromobenzoic acid

Participants

Reaction Conditions

Reaction Steps

Solid LiOH (5.04 g, 210 mmol) was added to a stirred solution of phenylmethyl 5-bromo-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 4, method C, 15 g, 37.8 mmol) in THF (150 ml) and water (50.0 ml) at 20° C. The reaction mixture was stirred at 71° C. overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (200 ml). 10% aqueous HCl was added to the mixture to adjust the pH to 2. The organic phase was isolated, washed with brine, dried over Na2SO4 and concentrated to give a white solid. The crude product was purified by silica gel chromatography eluting with hexane:ethyl acetate (3:1) to yield the title compound. 6.1 g.

Provenance & Evidence