Reaktion #50479

Reaktionsgleichung

(E,E)-farnesol

PBr3

→

bromide

(E,E) -3,7,11-Trimethyl-2,6,10-dodecatrienyl bromide

Lösungsmittel

ether

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with water
2. 2
   Sonstigeseparated
3. 3
   WaschenThe organic phase was washed with 5 mL of H2O, 5 mL of saturated NaHCO3, and 5 mL of brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Sonstigeevaporated

Vorschrift

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.

Quelle