Reaction #64428

Reaction equation

n-butyl lithium

1-bromopentane

triphenylphosphine

3-bromobenzaldehyde

→

3-bromo-(1-hexenyl)benzene

Solvents

hexane

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGThis mixture is stirred for 30 minutes
2. 2
   Concentrationand after concentrating
3. 3
   workup.ADDITIONdiluting with ether
4. 4
   Filtrationthe solids are filtered off
5. 5
   ConcentrationFurther concentration of the filtrate and chromatography over silica gel eluting with 3:2 hexane

Procedure

To 14.7 gm of the Wittig salt prepared from 1-bromopentane and triphenylphosphine in 80 ml of tetrahydrofuran at 0° C. is added 22.5 ml of n-butyl lithium (1.6M) in hexane. The mixture is stirred for 15 minutes, and 3.8 ml of 3-bromobenzaldehyde is added. This mixture is stirred for 30 minutes; and after concentrating and diluting with ether, the solids are filtered off. Further concentration of the filtrate and chromatography over silica gel eluting with 3:2 hexane:ether yields pure 3-bromo-(1-hexenyl)benzene as a clear oil.

Source