[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N+:22]([O-])=O)[CH2:5][N:6]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8]([C:15]([F:18])([F:17])[F:16])=[N:7]1.C([O-])(=O)C.[NH4+].CC(C)=O>[Cl-].[Cl-].[Cl-].[Ti+3].O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[NH2:22])[CH2:5][N:6]1[C:10]([C:11]([F:12])([F:13])[F:14])=[CH:9][C:8]([C:15]([F:18])([F:17])[F:16])=[N:7]1To a mixture of 1-(3-methyl-4-nitrobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (1.4 g), ammonium acetate (30.5 g), acetone (60 ml) and water (30 ml), 20% aqueous solution of titanium trichloride (27.5 g) was added at room temperature and the mixture was stirred at room temperature for 12 hours. After finishing the reaction, the mixture was extracted with ethyl acetate, washed with saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate. After distilling off the solvent, the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-aminobenzyl)-3,5-bis(trifluoromethyl)-1H-pyrazole (1.19 g).
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