Reaction #73765

Reaction equation

HCl

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

4-chlorophenylmagnesium bromide

→

desired product

Yield 91.0%

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

Yield 91.0%

Solvents

toluene

Conditions

Workup

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   Extractionextracted with ethyl acetate
3. 3
   OtherThe organic layer was separated
4. 4
   Dryingdried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   Otherthe crude product was purified over flash silica chromatography
8. 8
   Washeluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

Procedure

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.

Source