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

Participants

Reaction Conditions

Reaction Steps

Solid LiOH (1.01 g, 42.1 mmol) was added in a single charge to a stirred solution of phenylmethyl 5-bromo-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 4, method B; 3 g, 7.55 mmol) in a 3:1 mixture of THF and water (40 ml) at 20° C. The reaction mixture was stirred at 71° C. for 16 h. After cooling to room temperature, it 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 as white solid. 2.1 g.

Provenance & Evidence