Dimethylformamide → 3,4-Dibromothiophene-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (1.3 g, 12.5 mmol) in 15 mL of anhydrous THF was added n-BuLi (4.0 mL, 2.5 M in hexane) at −78° C. After the mixture was stirred at −78° C. for 0.5 h 3,4-dibromothiophene (2 g, 8.3 mmol) in anhydrous THF (20 mL) was added. The mixture was stirred at −78° C. for 15 min., a solution of DMF (670 mg, 9.2 mmol) in THF (5 mL) was added. After being stirred at this temperature for 0.5 h, the mixture was stirred at room temperature for 2 hours. The mixture was quenched with NH4Cl saturated solution, diluted with water, extracted with EtOAc, concentrated, and purified by column chromatography to give 3,4-dibromothiophene-2-carbaldehyde (1.0 g, yield 45%).

Provenance & Evidence