反应 #47533

反应方程式

3-chloro-but-2-enoic acid ethyl ester

Potassium t-butoxide

3-bromo-phenol

→

(E)-3-(3-bromo-phenoxy)-but-2-enoic acid ethyl ester

收率 39.0%

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   温度the reaction mixture was heated
2. 2
   温度to reflux for 0.75 h
3. 3
   温度The reaction mixture was refluxed for an additional 3 h
4. 4
   浓缩After this time, the mixture was concentrated in vacuo
5. 5
   workup.ADDITIONthe residue was diluted with water
6. 6
   萃取extracted with diethyl ether
7. 7
   洗涤The organic layer was then washed with 5% aqueous sodium hydroxide solution
8. 8
   干燥dried over sodium sulfate
9. 9
   浓缩concentrated in vacuo

实验过程

Potassium t-butoxide (10.5 g, 0.094 mol) was added to a stirred solution of 3-bromo-phenol (8.18 g, 0.047 mol) in tetrahydrofuran (30 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (prepared as in Example 191, 7.00 g, 0.047 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% aqueous sodium hydroxide solution followed by a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to afford (E)-3-(3-bromo-phenoxy)-but-2-enoic acid ethyl ester (5.20 g, 39%) as a yellow oil.

来源