Dimethylformamide → HCID 86696072, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, LDA (299.0 mL, 328.9 mmol) was slowly added dropwise, at −70° C. or lower, to a THF (400 mL) solution of compound (76) (89.7 g, 274.1 mmol). The reaction mixture was agitated at −70° C. or lower for 1 hour, and then DMF (30.1 g, 411.1 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 400 mL of 1N hydrochloric acid aqueous solution, and extracted with 200 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-(2-(4-propylcyclohexyl)ethyl)benzaldehyde (77) (61.4 g, yield 63.1%) was obtained.

Provenance & Evidence