Реакция #73765

Уравнение реакции

HCl

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

4-chlorophenylmagnesium bromide

→

desired product

Выход 91.0%

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

Выход 91.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ДругоеThe organic layer was separated
4. 4
   Сушкаdried (MgSO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   Другоеthe crude product was purified over flash silica chromatography
8. 8
   Промывкаeluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

Методика

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.

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