Hydrochloric Acid → 4-Fluoro-2-iodophenol

Participants

Reaction Conditions

Reaction Steps

Chloramine-T trihydrate (50 g, 178 mmol) was added to a stirred, cooled (0° C.) solution of 4-fluorophenol (20 g, 178 mmol) and sodium iodide (26.7 g, 178 mmol) in dimethylformamide (250 mL). The mixture was stirred at 0° C. for 1 h., and poured into water (1000 mL). The mixture was acidified with hydrochloric acid (1M) and extracted with ether (4×200 mL). The combined organic fractions were washed with aqueous sodium thiosulfate (5%, 3×100 mL), water (2×50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The reside was purified by flash column chromatography on silica gel, eluting with hexane/CH2Cl2 to give the title compound as an off-white solid (7.8 g, 18%). 1H NMR (360 MHz, CDCl3) δ 5.08 (1H, s), 6.90-7.01 (2H, m), and 7.37 (1H, dd, J 7.6, 2.9 Hz).

Provenance & Evidence