Carbon tetrabromide → 8-bromo-1-octyne

Participants

Reaction Conditions

Reaction Steps

Dehydrated dichloromethane (20 mL) and triphenylphosphine (5.91 g, 22.5 mmol) were added to 8-hydroxy-1-octyne (1.95 g, 15 mmol). The mixture was cooled to 0° C. and was then dropwise added to dehydrated dichloromethane (10 mL) containing carbon tetrabromide (7.46 g, 22.5 mmol), followed by stirring at room temperature for 2 hours. After separation between dichloromethane (100 mL) and 5% sodium bicarbonate (150 mL), the organic layer was washed with saturated brine (150 mL). The organic layer was dried over sodium sulfate and then concentrated. The concentrated product was purified by silica gel column chromatography (dichloromethane:methanol=from 100:0 to 99:1) to yield 8-bromo-1-octyne (crude).

Provenance & Evidence