[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH4+].[Cl-]>CO.O.[Fe]>[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1To a mixture of (2-bromo-3-fluoro-6-nitrophenyl)phenylamine (2.4 g, 7.7 mmol) in MeOH (40 mL) and water (15 mL) were added NH4Cl (2.38 g, 46.3 mmol) and iron powder (1.72 g, 30.9 mmol) and the reaction mixture heated at 90° C. for 1 h. After cooling to RT, the crude mixture was filtered through a pad of Celite® and the filtrate concentrated in vacuo. The resulting residue was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc (×3) and the combined organic fractions washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title compound (1.95 g, 90%). LCMS (Method C): RT 3.48 min [M+H]+ 281.1/283.1.
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