4-Bromo-2-fluorobenzaldehyde → HCID 86696069, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, potassium t-butoxide (30.4 g, 271.0 mmol) was added, at −30° C. or lower, to a THF (500 mL) suspension of iodotriphenyl((4-propylcyclohexyl)methyl)phosphine (73) (143.0 g, 271.0 mmol). The reaction mixture was agitated at −30° C. or lower for 1 hour, and then a THF (100 mL) solution of 4-bromo-2-fluorobenzaldehyde (50.0 g, 246.0 mmol) was added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 500 mL of water, and extracted with 200 mL of toluene three times. Combined organic layers were washed with 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 4-bromo-2-fluoro-1-(2-(4-propylcyclohexyl)vinyl)benzene (75) (75.0 g, yield 94.0%) was obtained.

Provenance & Evidence