The general procedure for the synthesis of 3-hydroxy-4-iodobenzyl alcohol from 3-hydroxy-4-iodobenzoic acid was as follows: to a solution of 3-hydroxy-4-iodobenzoic acid (20.9 g, 79.3 mmol) in anhydrous THF (160 mL) was slowly added a 1 M borane-THF solution (240 mL, 240 mmol). The reaction mixture was stirred at 60 °C for 2 hours. Upon completion of the reaction, the reaction was quenched by careful addition of water and subsequently extracted twice with ethyl acetate. The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting residue was washed with diisopropyl ether and hexane to give 3-hydroxy-4-iodobenzenemethanol (17.4 g, 88% yield) as a white solid. The structure of the product was confirmed by 1H NMR (CDCl3): δ 1.69 (br, 1H), 4.64 (s, 2H), 5.33 (s, 1H), 6.70 (dd, J = 7.8, 1.5 Hz, 1H), 7.01 (d, J = 1.5 Hz, 1H), 7.63 (d, J = 7.8 Hz, 1H).
