[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.[Br:9][C:10]1[CH:11]=[CH:12][C:13](F)=[C:14]([CH:17]=1)[CH:15]=[O:16]>[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([S:7][C:4]2[CH:5]=[CH:6][C:1]([CH3:8])=[CH:2][CH:3]=2)=[C:14]([CH:17]=1)[CH:15]=[O:16]p-Toluenethiol (0.12 g, 1.0 mmol) was dissolved in a 10% sodium hydroxide aqueous solution (1.7 mL), and tetrabutylammonium bromide (0.016 g, 0.05 mmol) was added thereto, followed by stirring at room temperature for 5 minutes. 5-Bromo-2-fluorobenzaldehyde (0.2 g, 1.0 mmol) dissolved in toluene (1.7 mL) was added thereto by dropping, followed by stirring at room temperature for 4 hours. After the conventional treatment, and was recrystallized and purified with ethanol and hexane, to give 5-bromo-2-[(4-methylphenyl)thio]benzaldehyde (0.23 g, 74.1%).
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