1. 5-bromo-2-chloro-4-fluorophenol (1.0 g, 4.4 mmol) was dissolved in N,N-dimethylformamide (DMF, 5 mL) in a dry reaction flask.
2. iodomethane (0.55 mL, 8.8 mmol) and potassium carbonate (1.2 g, 8.9 mmol) were added sequentially.
3. The reaction mixture was stirred at room temperature for 20 hours and the progress of the reaction was monitored by thin layer chromatography (TLC).
4. Upon completion of the reaction, the reaction was quenched by adding water (20 mL) to the reaction mixture.
5. The reaction mixture was extracted with ether (20 mL x 3) and the organic phases were combined.
6. The organic phase was washed with saturated saline (20 mL) and dried over anhydrous magnesium sulfate.
7. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain the crude product.
8. The crude product was further purified (if required) to give 5-bromo-2-chloro-4-fluoroanisole (0.951 g, 90% yield) as a white solid. 9.
9. The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3): δ3.88 (s, 3H), 7.07 (d, J=5.8 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H) and 19F-NMR (376 MHz, CDCl3): δ-116.1 (s, 1F).
