Phosphorus tribromide → (2E,6E)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene

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Reaction Steps

A solution of 1.00 g (4.5 mmol) of (E,E)-farnesol (Aldrich, further purified by flash chromatography) in 10 mL of distilled ether at 0° C. under argon in the dark was treated dropwise with a solution of 195 μL (2.05 mmol, 0.45 eq.) of PBr3 in 2 mL of diethyl ether (ether). The resultant mixture was stirred at 0° C. for one hour, then quenched with water and separated. The organic phase was washed with 5 mL of H2O, 5 mL of saturated NaHCO3, and 5 mL of brine, dried over Na2SO4 and evaporated to give 1.26 g (98%) of crude bromide as a clear oil.

Provenance & Evidence