General procedure for the synthesis of 2-fluoro-6-methoxyaniline using 3-fluoro-2-nitroanisole as starting material: 10% Pd/C catalyst (7.46 g, 70.1 mmol) and ethanol (400 mL) were added to a Parr reactor followed by 1-fluoro-3-methoxy-2-nitrobenzene (40.0 g, 234 mmol). The reactor was evacuated and filled with hydrogen (50 psi) and the reaction was shaken for 5 h under hydrogen atmosphere. After completion of the reaction, the catalyst was removed by Celite filtration and the filtrate was concentrated to give 2-fluoro-6-methoxyaniline (30.0 g, 83% yield) as a colorless oil. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.75 (broad single peak, 2H), 3.86 (single peak, 3H), 6.58-6.71 (multiple peaks, 3H); the molecular ion peak [M + H]+ = 142 was detected by LC-MS (LC-ES).
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