Reacción #553961

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 (decomposes).

Fuente