Dimethylformamide → 6-Bromo-2-fluoro-3-(4-propylcyclohexyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Under 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.

Provenance & Evidence