反応 #73765

反応方程式

HCl

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

4-chlorophenylmagnesium bromide

→

desired product

収率 91.0%

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

収率 91.0%

溶媒

toluene

反応条件

後処理

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   抽出extracted with ethyl acetate
3. 3
   その他The organic layer was separated
4. 4
   乾燥dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他the crude product was purified over flash silica chromatography
8. 8
   洗浄eluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

実験手順

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.

出典