Reacción #73765

Ecuación de reacción

HCl

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

4-chlorophenylmagnesium bromide

→

desired product

Rendimiento 91.0%

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

Rendimiento 91.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   OtroThe organic layer was separated
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   Otrothe crude product was purified over flash silica chromatography
8. 8
   Lavadoeluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

Procedimiento

A solution of 3-(4-bromo-phenyl)-2-cyano-acrylic acid ethyl ester (1.5 g, 5.36 mmol) in dry toluene (12 ml) was added dropwise to 4-chlorophenylmagnesium bromide (0.5 M solution in tetrahydrofuran, 6.96 ml, 6.96 mmol) at 0° C. The reaction mixture was heated to 85° C. for 3 hours, poured onto ice, acidified with 1N HCl 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 petroleum ether to ethyl acetate/petroleum ether (5:95) to afford the desired product (1.91 g, 91% yield). LC/MS: (PS-A2) Rt 3.78 [M+H]+ 391.93.

Fuente