Bromine → 5-Bromo-2-fluoro-4-hydroxybenzaldehyde

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To a solution of 2-fluoro-4-hydroxybenzaldehyde (2.2 g, 15.7 mmol, 1 eq) in acetic acid (70 mL) was added a solution of bromine (2.71 g, 17.0 mmol, 1.1 eq) in acetic acid (10 mL), and the mixture was stirred at 45° C. for 26 h. The reaction was concentrated in vacuo, brine (50 mL) was added, and the mixture was extracted with EtOAc (3×80 mL). The combined organic layers were dried (Na2SO4), concentrated in vacuo. The resultant residue was purified by silica gel chromatography (DCM:MeOH=15:1 to 5:1) to afford 1.2 g (35%) of 5-bromo-2-fluoro-4-hydroxybenzaldehyde (25).

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