反应 #47490

反应方程式

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

N-bromosuccinimide

benzoyl peroxide

→

(E)-4-bromo-3-(2-methylsulfanyl-phenoxy)-but-2-enoic acid ethyl ester

收率 38.0%

溶剂

carbon tetrachloride

反应条件

后处理

1. 1
   其他Nitrogen gas was bubbled through the mixture for 5 min
2. 2
   温度the resulting mixture was heated
3. 3
   温度to reflux for 4 h
4. 4
   其他was then placed in the refrigerator overnight
5. 5
   其他The solids formed
6. 6
   其他were removed by filtration
7. 7
   浓缩the filtrate concentrated in vacuo
8. 8
   其他The crude product obtained
9. 9
   其他was purified

实验过程

To a stirred mixture of (E)-3-(2-methylsulfanyl-phenoxy)-but-2-enoic acid ethyl ester (1.00 g, 0.004 mol) in carbon tetrachloride (15 mL) under a nitrogen atmosphere was added N-bromosuccinimide (1.00 g, 0.006 mol) and benzoyl peroxide (0.13 g, 0.001 mol). Nitrogen gas was bubbled through the mixture for 5 min, and the resulting mixture was heated to reflux for 4 h. The reaction mixture was then placed in the refrigerator overnight. The solids formed were removed by filtration and the filtrate concentrated in vacuo. The crude product obtained was purified using flash column chromatography (silica gel (100-200 mesh), ethyl acetate/hexanes) to afford (E)-4-bromo-3-(2-methylsulfanyl-phenoxy)-but-2-enoic acid ethyl ester (0.50 g, 38%) as a yellow oil: LR-ES-MS m/z calculated for C13H15BrO3S [M]+ 330, observed 333.

来源