Reacción #415080

Ecuación de reacción

(E,E)-farnesol

PBr3

→

bromide

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

Disolventes

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with water
2. 2
   Otroseparated
3. 3
   LavadoThe organic phase was washed with 5 ml of H2O, 5 ml of saturated NaHCO3, and 5 ml of brine
4. 4
   Secadodried over Na2SO4
5. 5
   Otroevaporated

Procedimiento

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 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. TLC Silica (2:8 ethyl acetate:Hexane) Rf=0.69.

Fuente