To a dry round bottom flask was added intermediate 2
(2.64 g, 15.42 mmol), 10% Pd/C (0.528 g), EtOH (20 mL), and THF (20 mL). Argon was
bubbled through the reaction mixture and then the atmosphere was replaced with H2. The
reaction was stirred overnight at room temperature. Filtered the reaction through a pad of celite
with EtOH/THF to give 4-amino-2-fluoro-5-methylphenol (3) as an off white solid (2.0 g, 92%).
1H NMR (500 MHz, DMSO-d6) δ 8.48 (s, 1H), 6.53 (d, J = 9.8 Hz, 1H), 6.38 (d, J = 13.2 Hz,
1H), 4.42 (s, 2H), 1.94 (s, 3H).
