Ethanol → Benzenamine, 2-bromo-5-chloro-3-methyl-

Participants

Reaction Conditions

Reaction Steps

2-Bromo-5-chloro-1-methyl-3-nitro-benzene (721 mg, 3.5 mmol, Example 135: step b) was dissolved into EtOH (6 mL). To this was added ammonium chloride (1.9 g, 35 mmol) dissolved into water (10 mL). The reaction was heated to 50° C., iron (9.6 mg, 0.34 mmol) was added and the reaction was then heated to 80° C. for 12 hours. The reaction mixture was filtered through celite, washed with methanol and EtOAc and the solvents were removed in vacuo. The residue was dissolved into EtOAc and washed with brine to remove salts. The organic layers were dried (MgSO4) and the solvents were removed in vacuo resulting in the title compound (595 mg, 78%) as a brown solid. 1H-NMR (CDCl3): δ 6.63–6.61 (m, 2H), 2.33 (s, 3H).

Provenance & Evidence