[Cl-].[NH4+:2].[Br:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1CN.[CH3:16]O.O>[Fe]>[Br:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=1[NH:2][CH3:16]Ammonium chloride (6.24 g, 117 mmol) and iron powder (4.34 g, 77.7 mmol) were added to a stirred mixture of (2-bromo-3-fluoro-6-nitrophenyl)methylamine (4.84 g, 19.4 mmol) in 3:1 methanol/water (320 mL) and the resultant mixture heated at reflux for 24 h. The solid material was removed by filtration and the filtrate concentrated to approximately ⅓ volume. This mixture was partitioned between DCM (3×) and water then the combined DCM extracts were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by chromatography (SiO2, eluting with 0-5% methanol in DCM) to give title compound as an oil (1.99 g, 47%). LCMS (Method C): RT 2.37 min [M+H]+ 219.0, 221.0
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