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

Temperature

0 °C

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.

1. customThe reaction was quenched by addition of ice cold water
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with ether
4. washThe combined organic extracts were washed with NaHCO3 and brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-f37544afe3e44f0aa30a55cfab8c4a6e

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012693B2