4-Bromo-3-methyl-2-nitrophenol → 2-amino-4-bromo-3-methylphenol

Participants

Reaction Steps

4-Bromo-3-methyl-2-nitrophenol (10 g, 43.1 mmol) was dissolved in methanol (254 ml), purged with nitrogen and loaded with Pt/C (1.013 g, 10.13 mmol). The reaction was stirred under 60 psi of hydrogen for 5 hours. When complete, the reaction was filtered carefully on Celite™. The top was covered by more Celite™, flushed with ethyl acetate and dichloromethane and allowed to dry a bit before adding more. The organics were concentrated and 2-amino-4-bromo-3-methylphenol (8.6 g, 99%) was isolated as a brown solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.67 (d, J=9.0 Hz, 1 H), 6.93 (d, J=9.0 Hz, 1 H), 2.63 (s, 3 H); LC/MS (m/z) ES+=202 (M+1).

Provenance & Evidence