Furfural → 2-(2,2-Dibromovinyl)furan

Participants

Reaction Steps

Carbon tetrabromide (20 mmole) was dissolved in anhydrous diohloromethane (200 mL), and kept at 20° C. under argon atmosphere. Triphenylphosphine (20 mmole) in dichloromethane (200 mL) was added dropwise. After 15 minutes of stirring, the reaction flask was kept at −60° C., followed by the addition of furaldehyde (10 mmole) and triethylamine (10 mmole) in dichloromethane (100 mL). The reaction mixture was brought to room temperature, and two volumes of ether were added. The precipitate was filtered, and the filtrate was dried. The crude material was purified by Si gel column chromatography (>50% yield).

Provenance & Evidence