Carbon tetrabromide → HCID 10858994, compound

Participants

Reaction Steps

To a mixture of 1-(4-isobutylphenyl)pentanol and carbon tetrabromide in tetrahydrofuran was added triphenylphosphine, and the mixture was stirred at room temperature for 30 minutes. Insoluble materials were removed by filtration and the filtrate was concentrated. Hexane was added to the residue and the mixture was filtered again. Concentration of the filtrate gave crude 1-bromo-1-(4-isobutylphenyl)pentane. Sodium was added portionwise to ethylene glycol at 80° C. while stirring. To the resultant solution was added the obtained crude 1-bromo-1-(4-isobutylphenyl)pentane, and the mixture was stirred at 120° C. for 1 hour. After the mixture was cooled, diluted hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated. Silica gel column chromatography of the concentrate afforded the object compound.

Provenance & Evidence