Reacción #48048

Ecuación de reacción

4-iodobenzonitrile

sodium pentafluoroproprionate

DMF

→

title compound

Rendimiento 52.3%

4-pentafluoroethyl-benzonitrile

Rendimiento 52.3%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto distil off
2. 2
   TemperaturaAfter cooling
3. 3
   workup.ADDITIONethyl acetate (200 mL) was added
4. 4
   Filtraciónthe mixture was filtered through diatomaceous earth
5. 5
   Otrothe filtrate was partitioned between ethyl acetate/heptane and water
6. 6
   LavadoThe organic layer was washed with brine
7. 7
   Secadodried (MgSO4)
8. 8
   Otroevaporated

Procedimiento

A mixture of 4-iodobenzonitrile (10.0 g, 43.7 mmol), sodium pentafluoroproprionate (15.4 g, 82.9 mmol), and copper(I) iodide (16.6 g, 87.3 mmol), DMF (160 mL), and toluene (60 mL) was heated at 160° C. for 16 h, allowing most of the toluene to distil off. After cooling, ethyl acetate (200 mL) was added, and the mixture was filtered through diatomaceous earth, and the filtrate was partitioned between ethyl acetate/heptane and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (5.05 g 52%). Yellow oil, MS (EI) 221.1 (M+).

Fuente