[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>O.ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:15]=[C:16]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=12.1 g (5.7 mmol) of N-[2-(4-bromophenylamino)phenyl]benzamide were suspended into 30 mL of xylene, 0.6 g (2.9 mmol) of p-toluenesulfonic acid monohydrate was added, and the whole was refluxed under heating for 3 hours. After the resultant had been stood to cool, the reaction solution was added with ethyl acetate, dichloromethane, and water for filtering insoluble matter out. An organic layer was extracted from a mother liquor, washed with water and a saturated sodium chloride solution, and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography to obtain 1.0 g of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole (52% yield).
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