(S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran

915095-87-3

915095-94-2

(2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone (50 g, 116.5 mmol) was added to a 500 mL three-necked flask equipped with a thermometer, a reflux condenser, and a drying tube with THF (350 mL) and stirred at room temperature. Subsequently, NaBH4 (22.0 g, 582.5 mmol) and AlCl3 (39 g, 291.5 mmol) were added in batches, and vigorous bubbling was maintained during the reaction. After the addition was completed, the reaction mixture was heated and refluxed for 5 h. The progress of the reaction was monitored by TLC, and the reaction was stopped after confirming the complete conversion of the raw materials. After the reaction system was cooled to room temperature, it was slowly poured into a mixture consisting of 200 mL of ice water and 75 mL of 2M HCl with vigorous stirring for 30 min. After standing and layering, the aqueous phase was extracted with ethyl acetate (100 mL x 3). The organic phases were combined and washed sequentially with sodium bicarbonate solution to neutral, saturated sodium chloride solution (200 mL), dried and concentrated to give a light yellow solid crude product. The crude product was dissolved in a mixed solvent of 50 mL of water and 10 mL of ethanol and crystallized to give the white solid product (S)-3-(4-(2-chloro-5-iodophenyl)phenoxy)tetrahydrofuran (26.6 g) in 90% yield.