Diisopropylamine → HCID 86707392, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N,N-diisopropylamine (680 μL, 5.19 mmol) in tetrahydrofuran (5 ml) was added dropwise a solution of 1.67 mol/L n-butyllithium in hexane (3.11 ml, 5.19 mmol) at −78° C. under argon atmosphere, and the mixture was stirred at the same temperature for 15 minutes. The reaction solution was slowly warmed to 0° C., and stirred for 20 minutes, and then cooled to −40° C. Then, thereto was added dropwise a solution of 3-bromo-2-(trifluoromethyl)thiophene (1000 mg, 4.33 mmol) in tetrahydrofuran (15 ml). The mixture was stirred at the same temperature for 20 minutes, and the reaction solution was slowly warmed to −10° C., and then stirred for 5 minutes. The reaction solution was cooled to −40° C., and then thereto was added dropwise N,N-dimethylformamide (1 mL). Then, the mixture was slowly warmed to 0° C., and stirred overnight. To the reaction solution was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→9:1) to give 4-bromo-5-(trifluoromethyl)thiophene-2-carbaldehyde (527 mg, 47%) as a yellow oil.

Provenance & Evidence