To a solution of acetone (10 mL) containing 4-chloro-3-fluorophenol (500 mg, 3.41 mmol) was added potassium carbonate (942.59 mg, 6.82 mmol) and iodomethane (1.94 g, 13.64 mmol). The reaction mixture was stirred at 60 °C for 16 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio of petroleum ether:ethyl acetate = 20:1) to confirm the completion of the reaction. After completion of the reaction, the mixture was concentrated to remove the solvent. Water (20 mL) was added to the residue and extracted with ethyl acetate (20 mL x 3). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 4-chloro-3-fluoroanisole (470 mg, 2.93 mmol, 85.84% yield) as a colorless oil.
