Reacción #586122

Ecuación de reacción

water

2-mercapto-4-(4-trifluoromethylphenyl)benzonitrile

potassium tert-butoxide

→

2-(2-propenylthio)-4-(4-trifluoromethylphenyl)benzonitrile

Rendimiento 43.5%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   Extracciónextracted with 50 ml of ethyl acetate twice
3. 3
   LavadoThe ethyl acetate layer was washed with 50 ml of water twice
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
6. 6
   OtroPurification of the residue by silica gel column chromatography

Procedimiento

1.0 g (3.6 mmol) of 2-mercapto-4-(4-trifluoromethylphenyl)benzonitrile, 0.45 g (4.0 mmol) of potassium tert-butoxide and 0.5 g (4.1 mmol) of 3-propenyl bromide were stirred in 20 ml of N,N-dimethylformamide at room temperature for 1 hour. The resulting reaction mixture was poured into 20 ml of water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.5 g of 2-(2-propenylthio)-4-(4-trifluoromethylphenyl)benzonitrile (yield 43.0%) as yellow crystals (m.p. 89-90° C.).

Fuente