Reaction #50094

Reaction equation

α-allyl-α-isopropyl-3,4-dimethoxy- benzyl cyanide

azobisisobutyronitrile

hydrogen bromide

potassium carbonate

hydrogen bromide

→

crude product

Yield 94.0%

5-Bromo-2-(3,4-dimethoxyphenyl)-2- isopropyl valeronitrile

Yield 94.0%

Solvents

cyclohexane

n-hexane

Conditions

Workup

1. 1
   WashThe separated cyclohexane solution of the product was washed with water until neutral pH
2. 2
   OtherAfter drying
3. 3
   Otherevaporating the solvent under diminished pressure

Procedure

To a solution of 50 g of α-allyl-α-isopropyl-3,4-dimethoxy- benzyl cyanide and 2 g of azobisisobutyronitrile in 400 ml of cyclohexane (or n-hexane) gaseous hydrogen bromide was introduced for 70 minutes, when, according to GLC, the reaction mixture did not contain the starting allyl derivative. During the introduction of the hydrogen bromide, the reaction temperature raised to 40° C. The reaction mixture was neutralized with 200 ml of 30% solution of potassium carbonate. The separated cyclohexane solution of the product was washed with water until neutral pH. After drying and evaporating the solvent under diminished pressure, the crude product (61.7 g, 94%) was obtained, which could be used without purification in further reaction step.

Source