General procedure for the synthesis of 1-(chloromethyl)-3-iodobenzene from 3-iodobenzyl alcohol: 3-iodobenzyl alcohol (600 mg, 2.56 mmol) was dissolved in dichloromethane (DCM, 3 mL), and thionyl chloride (3 mL, 41.3 mmol) was added, and the reaction was stirred for 18 hours at room temperature. Subsequently, thionyl chloride (1 mL, 13.7 mmol) was added and the reaction mixture was heated to reflux for 12 hours. Upon completion of the reaction, the cooled solution was alkalized with 50% sodium hydroxide solution, diluted with water and extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give a clarified slurry. After standing, the slurry crystallized to give 3-iodobenzyl chloride as a white solid (650 mg, quantitative yield).
