Dimethylformamide → 5-Bromo-4-methylthiophene-2-carbaldehyde

Participants

Reaction Steps

Phosphoryl chloride (5.3 ml, 0.57 mmol) was added dropwise to N,N-dimethylformamide (8.8 ml, 0.11 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. 2-Bromo-3-methylthiophene (5.00 g, 28.2 mmol) was added dropwise thereto under ice-cooling and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was neutralized with a 2N aqueous sodium hydroxide solution under ice-cooling. The reaction mixture was extracted with diethyl ether and the organic layer was dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1) to give 5-bromo-4-methyl-2-thiophenecarbaldehyde (1.41 g, yield: 24%).

Provenance & Evidence