Boron tribromide → 4-Hydroxy-2,5-dimethylbenzoic acid

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Reaction Steps

Boron tribromide solution (1M in DCM, 7.21 mL) was added dropwise to suspension of 4-methoxy-2,5-dimethylbenzoic acid (1 g) in DCM (5 mL) at −78° C. The reaction was allowed to warm to RT and stirred overnight. The reaction was cooled to −78° C. and boron tribromide solution (1M in DCM, 7.21 mL) was added. The reaction was allowed to warm to RT and stirred overnight. The reaction was cautiously poured onto ice (˜50 mL). The resulting aqueous solution was extracted with DCM (5×50 mL). The organic solutions were combined, washed with brine (50 mL), dried over magnesium sulphate, filtered and evaporated to give the subtitled compound as a tan solid. Yield 0.75 g.

Provenance & Evidence