Water → 5-(Hydroxymethyl)-2-iodophenol

To a solution of 3-hydroxy-4-iodobenzoic acid (20.9 g, 79.3 mmol) in anhydrous THF (160 mL) was added 1 M borane THF solution (240 mL, 240 mmol) by small portions, and the mixture was stirred at 60° C. for 2 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with diisopropyl ether and hexane to give the title compound (17.4 g, yield 88%) as a white solid.