[F:1][CH:2]([F:13])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1.Cl.C(=O)(O)[O-].[Na+]>CO.O.[Fe]>[F:13][CH:2]([F:1])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([CH:4]=1)[NH2:10]To a solution of 4-(difluoromethyl)-1-fluoro-2-nitrobenzene (0.200 g, 1.04 mmol) in methanol (10 mL) was added iron powder (0.500 g, 8.92 mmol). The reaction mass was cooled at 0° C. followed by drop-wise addition of conc. HCl (3.0 mL). The reaction mass was stirred at RT for 1 h. The reaction mass was diluted with water and basified with sodium bicarbonate, extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.150 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 5.44 (s, 2H), 6.67 (m, 1H), 6.86 (s, 1H), 6.93 (d, J=8.1 Hz, 1H), 7.05-7.12 (m, 1H); MS [M+H]+: 160.13.
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