Phosphorus tribromide → 2,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Participants

Reaction Conditions

Reaction Steps

10.02 g (64.96 mmol) geraniol was dissolved in 120 ml of dry THF. At 0° C., 3.1 ml (8.93 g, 32.98 mmol) PBr3 were added drop wise via septum and syringe and the clear, colorless solution was stirred at 0° C. for 3 h. The reaction was quenched by addition of ice cold water. The layers were separated and the aqueous layer was extracted with ether. The combined organic extracts were washed with NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo to give geranyl bromide as a colourless oil (13.59 g, 62.63 mmol, 96%). The crude product was used for the next step without further purification.

Provenance & Evidence