GENERAL PROCEDURE: A freshly prepared sodium methanol solution [prepared by dissolving 0.58 g (25 mmol) of sodium metal in 3 mL of anhydrous methanol] was slowly added dropwise to 30 mL of anhydrous methanol solution containing 2 g (11.2 mmol) of 2,3,4-trifluoronitrobenzene. The reaction was carried out at 40 °C and under nitrogen protection. The resulting mixture was stirred at room temperature overnight and the reaction was subsequently quenched with 1 M aqueous citric acid (0.1 equiv). Methanol was removed by evaporation under reduced pressure and the residue was dissolved in ether, washed sequentially with 1M aqueous citric acid and saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 2.2 g (99% yield) of the crude product 2,6-dimethoxy-3-nitromonofluorobenzene, which was finally purified by recrystallization from hexane. The product was characterized by H1 NMR (CDCl3): δ 3.95 (s, 3H, OMe); 4.06 (d, 3H, J = 1.6 Hz); 6.72 (dd, 1H, J = 9.4 Hz, J = 7.5 Hz); 7.72 (dd, 1H, J = 9.4 Hz, J = 2.23 Hz).
