GENERAL STEPS: Iodomethane (850 μL, 13.646 mmol) and potassium carbonate (943 mg, 6.824 mmol) were sequentially added to a solution of tetrahydrofuran (10 mL) containing 2-chloro-6-fluorophenol (1.0 g, 6.824 mmol). The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the mixture was transferred to a partition funnel and extracted with ether (50 mL) and water (50 mL) by partition. The organic phase was separated and washed with water (2 x 20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-chloro-6-fluoroanisole as a colorless liquid in 94% yield (1.03 g).1H NMR (400 MHz, CD3OD) δ: 3.90-3.91 (s, 3H), 7.01-7.12 (m, 2H), 7.18-7.21 (m, 1H).
