반응 #73765

반응 방정식

HCl

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

4-chlorophenylmagnesium bromide

→

desired product

수율 91.0%

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

수율 91.0%

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   추출extracted with ethyl acetate
3. 3
   기타The organic layer was separated
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타the crude product was purified over flash silica chromatography
8. 8
   세척eluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

실험 절차

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.

출처