Bromine → 3-Bromo-5-fluoro-4-hydroxybenzaldehyde

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To a solution of 3-fluoro-4-hydroxybenzaldehyde (2 g, 14.3 mmol, 1 eq, Oakwood Products, Inc., West Columbia, S.C., USA) in acetic acid (60 mL), was added a solution of bromine (2.7 g, 17.0 mmol, 1.2 eq) in acetic acid (10 mL), and the mixture was stirred at 45° C. for 26 h. After concentration in vacuo, brine (50 mL) was added to the residue and the mixture was extracted with EtOAc (3×80 mL). The combined organic layers were dried (Na2SO4), concentrated in vacuo, and purified by reversed phase semi-preparative .HPLC to afford 1.5 g (48%) of 3-bromo-5-fluoro-4-hydroxybenzaldehyde (26).

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