[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][C:9]=1[F:10])([O-])=O.Cl.C(=O)(O)[O-].[Na+].C(OCC)C>CO.[Fe]>[F:10][C:9]1[CH:8]=[CH:7][C:6]([C:11]([F:12])([F:13])[F:14])=[CH:5][C:4]=1[NH2:1]Twenty grams of 3-nitro-4-fluorobenzotrifluoride was dissolved in 50 ml of methanol. An iron powder (16 g) was added and concentrated hydrochloric acid was added dropwise with stirring. The reaction mixture was stirred overnight, followed by addition of sodium bicarbonate for neutralization. Then diethyl ether was added, and the insolubles were filtered off with cerite. The ether phase was separated, dried and concentrated under reduced pressure, giving 14 g of the contemplated product (yield 82%).
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