Boron tribromide → 2-Fluoro-4,6-dihydroxybenzaldehyde

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Reaction Steps

To a solution of 2-fluoro-4,6-dimethoxybenzaldehyde (3.68 g, 20.0 mmol) in dichloromethane (50 mL) was added dropwise boron tribromide (12.50 g, 50.0 mmol) at −78° C. The reaction was stirred at room temperature overnight and poured into ice. The resulting mixture was extracted with ethyl acetate (3×60 mL) and the combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/6) on silica gel to give the title compound as a white solid. (2.31 g, Yield: 76.4%). 1H NMR (400 MHz, DMSO-d) δ 11.53 (s, 1H), 11.22 (s, 1H), 9.99 (s, 1H), 6.16-6.24 (m, 2H). MS (ESI) m/z=157 [M+H]+.

Provenance & Evidence