[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.CN(C)[CH:36]=[O:37]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)[C:16]2[CH:21]=[CH:20][C:19]([CH:36]=[O:37])=[CH:18][CH:17]=2)=[CH:6][CH:7]=1
In an argon atmosphere, tris(4-bromophenyl)amine (964 mg, 2.00 mmol) was dissolved in tetrahydrofuran (10 mL) and cooled to −78° C. n-Butyl lithium (a 1.6 mol/L hexane solution, 1.5 mL, 2.4 mmol) and dimethylformamide (0.19 mL, 2.4 mmol) was dripped thereto at a system temperature of −60° C. or less, followed by stirring for 10 minutes. To the reaction liquid was added water and the product was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=8/1) to give 4-[bis(4-bromophenyl)amino]benzaldehyde (377 mg, 44%).
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