General procedure for the synthesis of 4-hydroxy-3-iodobenzaldehyde from 4-hydroxybenzaldehyde: To a stirred solution of 4-hydroxybenzaldehyde (2.0 g, 16.39 mmol) in acetic acid (30 mL) was added N-iodosuccinimide (4.5 g, 19.67 mmol). The reaction mixture was stirred at room temperature for 16 hours and then filtered. The filtrate was poured into water (100 mL) and ethyl acetate (50 mL) was added. The aqueous phase was separated and then extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, washed with water (2 × 20 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (2.0 g, 50% yield) as a white solid, which was ready to be used without further purification.LCMS (ES-) m/z 247.1 ([M-H]-) with a retention time of 1.44 min (Method 9).
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