[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]2)=[C:12]([F:25])[CH:11]=1.CN([CH:29]=[O:30])C>C1COCC1>[Br:9][C:10]1[C:11]([CH:29]=[O:30])=[C:12]([F:25])[C:13]([CH:16]2[CH2:17][CH2:18][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:20][CH2:21]2)=[CH:14][CH:15]=1Under a nitrogen atmosphere, LDA (11.6 mL, 12.87 mmol) was slowly added dropwise, at −70° C. or lower, to a THF (30 mL) solution of compound (70) (3.5 g, 11.70 mmol). The reaction mixture was agitated at −70° C. or lower for 1 hour, and then DMF (1.28 g, 17.55 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 50 mL of 1 N hydrochloric acid aqueous solution, and extracted with 20 mL of toluene three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 6-bromo-2-fluoro-3-(4-propylcyclohexyl)benzaldehyde (71) (2.3 g, yield 89.7%) was obtained.
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