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With iron; ammonium chloride In ethanol; water at 85℃; for 1 h;
l,2-dichloro-3-fluoro-5-nitro-benzene (5 g, 23.8 mmol), NH4C1 (14 g, 261.9 mmol) was dissolved in EtOH/H2O(160 mL, 15/1). The solution heated to 85°C followed by addition of Fe in portions. After additon the reaction mixture was heated( 85°C) for lh. The reaction mixture was extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine (15 mL), dried over Na2S04, and concentrated in vacuum to give crude product. Purification by flash chromatography gave 3,4- dichloro-5-fluoro-aniline (4 g).