Dimethylformamide → 6-Bromo-2-fluoro-3-propylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, LDA (50.7 mL, 56.25 mmol) was slowly added dropwise, at −70° C. or lower, to a THF (100 mL) solution of 4-bromo-2-fluoro-1-propylbenzene (50) (11.1 g, 51.13 mmol). The reaction mixture was agitated at −70° C. or lower for 1 hour, and then DMF (6.15 g, 76.70 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 100 mL of 1N hydrochloric acid aqueous solution, and extracted with 60 mL of toluene 3 times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over magnesium sulfate and a solvent was distilled off by evaporator. The residue was purified by silica gel column chromatography, and thus 6-bromo-2-fluoro-3-propylbenzaldehyde (51) (5.0 g, yield 36%) was obtained.

Provenance & Evidence