C(O)(=O)C.O.[Cl:6][C:7]1[CH:8]=[C:9]([N+:18]([O-])=O)[CH:10]=[C:11]([C:14]([F:17])([F:16])[F:15])[C:12]=1[F:13]>C(O)(=O)C.C(OCC)(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH:10]=[C:11]([C:14]([F:17])([F:15])[F:16])[C:12]=1[F:13])[NH2:18]In a mixture of 7.0 g of reduced iron, 4 mL of acetic acid and 50 mL of water, a solution of 6.0 g of 5-chloro-6-fluoro-3-nitrobenzotrifluoride in 80 mL of acetic acid-ethyl acetate (1:1) was added dropwise at 80° C. with stirring over 30 minutes. After the completion of the addition dropwise, it was continued to stir at the same temperature further for 1 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, insoluble material was filtered off through Celite, the organic phase was collected and washed with 100 mL of water and then 100 mL of saturated sodium hydrogen carbonate aqueous solution. The organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.0 g of the crude aimed product as red-brown oily substance. The resulting product was used as such without purification for the next step.
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