Reaction #8216

Reaction equation

bromoacetonitrile

indole

NaH

→

indol-1-yl-acetonitrile

Yield 27.1%

Solvents

ethyl acetate

dimethylformamide

Conditions

Workup

1. 1
   Washwashed with H2O (3×200 ml)
2. 2
   DryingThe organic layer is dried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   OtherThe crude residue is purified by flash chromatography (SiO2

Procedure

A 0° C. solution of indole (7 g, 59.8 mmol) in 200 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 3.1 g, 77.7 mmol). After 20 minutes, bromoacetonitrile (4.2 ml, 59.8 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir overnight. The reaction mixture is diluted with ethyl acetate (500 ml) and washed with H2O (3×200 ml). The organic layer is dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2; 5% then 20% ethyl acetate in hexanes) to give 2.53 g of indol-1-yl-acetonitrile (27%).

Source