2339-58-4

7087-60-7

7440-66-6

2339-58-4

Step 2. Synthesis of 3-fluoro-5-methoxyaniline. 3-Fluoro-5-nitroanisole (170, exact mass not provided) was dissolved in methanol (25 mL) and zinc powder (1.96 g, 30 mmol) and saturated ammonium chloride solution (20 mL) added in portions were added sequentially. The reaction mixture was stirred vigorously at room temperature for 5 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove insoluble impurities. The filtrate was concentrated under reduced pressure to remove the solvent. The concentrated residue was subjected to liquid-liquid extraction with ethyl acetate (25 mL) and saturated saline (20 mL). The organic phase was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a 3:1 (v/v) hexane/ethyl acetate solvent mixture to afford 3-fluoro-5-methoxyaniline (171) as a yellow solid (0.404 g, 54% yield).