Reaction #1328415

Reaction equation

allyl bromide

6-chlorobenzaldehyde

n-butyllithium

n-butyllithium

copper(I) cyanide

ammonium chloride

trimethylethylenediamine

→

2-Allyl-6-chlorobenzaldehyde

Solvents

hexane

hexane

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe mixture was cooled to −200° C.
2. 2
   workup.STIRRINGthe mixture was stirred at −10° C. for 30 minutes
3. 3
   workup.STIRRINGThe mixture was stirred at 0° C. for another 2.5 hours
4. 4
   OtherThe resulting solid was separated off
5. 5
   Extractionthe aqueous phase was extracted with diethyl ether
6. 6
   WashThe combined organic phases were then washed with saturated ammonium chloride solution
7. 7
   Otherdried
8. 8
   Otherthe solvent was removed under reduced pressure

Procedure

Under an atmosphere of protective gas, a solution of 10.89 g (0.107 mol) of trimethylethylenediamine in 50 ml of anhydrous tetrahydrofuran was cooled to −10° C. and admixed dropwise with 66.6 ml of a 1.6 molar solution of n-butyllithium in hexane (0.107 mol). After 10 minutes, 15 g (0.107 mol) of 6-chlorobenzaldehyde in 70 ml of tetrahydrofuran were added dropwise, and the mixture was admixed with a further 0.214 mol of n-butyllithium in hexane (146.8 ml) and stirred at 0° C. for 2.5 hours. The mixture was cooled to −200° C., 12.42 g (0.139 mol) of copper(I) cyanide were added, the mixture was stirred at −10° C. for 30 minutes, and 28.42 g of allyl bromide in 100 ml of tetrahydrofuran were then added dropwise. The mixture was stirred at 0° C. for another 2.5 hours, and 230 ml of saturated ammonium chloride solution were then added dropwise. The resulting solid was separated off and the aqueous phase was extracted with diethyl ether. The combined organic phases were then washed with saturated ammonium chloride solution and dried, and the solvent was removed under reduced pressure. This gave 17.0 g of 2-allyl-6-chlorobenzaldehyde (89%) in the form of a dark oil.

Source