Sodium Hydroxide → 2-(Benzyloxy)-4-bromo-5-methylbenzoic Acid

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Reaction Conditions

Reaction Steps

To a solution of 1-{4-bromo-5-methyl-2-[(phenylmethyl)oxy]phenyl}ethanone (may be prepared as described in Description 11; 607 mg, 1.90 mmol) in 1,4-dioxane (10 ml) was added sodium hydroxide (761 mg, 19.02 mmol) in water (10 ml). The solution was cooled to 0° C. and bromine (0.29 ml, 5.71 mmol) was added. The mixture was stirred for 10 minutes at 0° C. and then at room temperature for one hour. The dioxane was removed under reduced pressure and the residue acidified to pH=2 using 2N HCl. The mixture was extracted with ethyl acetate (3×20 ml), dried (MgSO4) and the solvent removed in vacuo to yield the title compound. 611 mg.

Provenance & Evidence