Reacción #73766

Ecuación de reacción

3-(4-bromo-phenyl)-3-(4-chloro-phenyl)-2-cyano-propionic acid ethyl ester

acetic acid

sulfuric acid

→

desired product

Rendimiento 50.0%

3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid

Rendimiento 50.0%

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawere refluxed for 2 hours
2. 2
   OtroReaction mixture
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   OtroThe organic layer was separated
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   Otrothe crude product was purified over flash silica chromatography
9. 9
   Lavadoeluting with ethyl acetate/petroleum ether (1:1)

Procedimiento

A mixture of 3-(4-bromo-phenyl)-3-(4-chloro-phenyl)-2-cyano-propionic acid ethyl ester (1.91, 4.87 mmol), acetic acid (10 ml), concentrated sulfuric acid (5 ml) and water (5 ml) were refluxed for 2 hours. Reaction mixture was poured into iced water and extracted with ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated, the crude product was purified over flash silica chromatography eluting with ethyl acetate/petroleum ether (1:1) to afford the desired product (0.82 g, 50% yield). LC/MS: (PS-A2) Rt 3.39 [M+H]+ 338.86.

Fuente