تفاعل #73765

معادلة التفاعل

HCl

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

4-chlorophenylmagnesium bromide

→

desired product

المردود 91.0%

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

المردود 91.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONpoured onto ice
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   أخرىThe organic layer was separated
4. 4
   تجفيفdried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىthe crude product was purified over flash silica chromatography
8. 8
   غسيلeluting with petroleum ether to ethyl acetate/petroleum ether (5:95)

الإجراء التجريبي

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.

المصدر