Reaction #93584

Reaction equation

2-(3,4-dimethoxyphenyl)-2-isopropylacetonitrile

sodium amide

1-bromo-3-chloropropane

→

2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile

2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)-acetonitrile

Solvents

toluene

toluene

Conditions

Workup

1. 1
   Temperaturethe resulting mixture warmed to 80°-90° C. for one hour
2. 2
   Extractionextracted with CH2Cl2, and vacuum
3. 3
   workup.DISTILLATIONdistilled

Procedure

A solution of 2-(3,4-dimethoxyphenyl)-2-isopropylacetonitrile (6a) in toluene is slowly added to sodium amide (1.5 eq) in toluene, and the resulting mixture warmed to 80°-90° C. for one hour. The mixture was then cooled to 15° C. and 1-bromo-3-chloropropane (2 eq) slowly added and stirred for two hours at room temperature. The mixture is then carefully poured into ice water, extracted with CH2Cl2, and vacuum distilled to yield 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)acetonitrile (21, b.p. 160°-165°/0.05 mmHg).

Source