General procedure: a mixture of 4-fluoro-2-methyl-5-nitrophenol (1.4 g, 8.2 mmol) and 10% Pd/C (0.3 g, 20% w/w) in methanol (80 mL) was stirred for 2 hours under hydrogen atmosphere (30 psi). Upon completion of the reaction, the Pd/C catalyst was removed by filtration and the filtrate was concentrated to afford 5-amino-4-fluoro-2-methylphenol (0.68 g, 62% yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 8.75 (s, 1H), 6.62 (d, J = 12.0 Hz, 1H), 6.21 (d, J = 8.1 Hz, 1H), 4.69 (s, 2H), 1.93 (s, 3H).
