[H-].[Na+].[OH:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.[Cl:10][C:11]1[CH:12]=[C:13]([C:21]([F:24])([F:23])[F:22])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1F.Cl>CN(C=O)C>[Cl:10][C:11]1[CH:12]=[C:13]([C:21]([F:23])([F:24])[F:22])[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[O:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1Sodium hydride (60% in oil, 0.44 g, 11.0 mmol) was added to a solution of 3-hydroxy-5-methylpyrazole (0.98 g, 10.0 mmol) and 3-chloro-4-fluoro-5-nitrobenzotrifluoride (1.5 g, 10.0 mmol) in DMF (30 ml), and the mixture was stirred under heating at 60° C. for 7 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid (80 ml) and extracted with ethyl acetate (30 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/7→1/3), to give a yellowish solid of 3-(2-chloro-6-nitro-4-trifluoromethylphenyloxy)-5-methylpyrazole (1.8 g, yield: 56.6%). mp: 120-123° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.29 (s, 3H), 5.79 (s, 1H), 7.98 (d, J=1.8 Hz, 1H), 8.17 (d, J=1.8 Hz, 1H), 8.65-9.30 (br s, 1H).
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