Ammonium Chloride → 2-Bromo-3-methylaniline

Participants

Reaction Steps

The procedure as in Example 20: step c was followed using 2-bromo-1-methyl-3-nitro-benzene (1 g, 4.6 mmol dissolved in 12 mL EtOH, Aldrich Chemical Company), ammonium chloride (2.5 g, 46 mmol dissolved in 6 mL H2O) and iron (1.3 g, 23 mmol). The title compound was obtained (1.0 g, quantitative yield) which was used without further purification. 1H-NMR (CDCl3): δ 6.95–7.00 (t, 1H, J=7.6 Hz), 6.60–6.65 (dd, 2H, J=8.1, 4.4 Hz), 4.10 (br s, 2H), 2.35 (s, 3H).

Provenance & Evidence