Реакция #47534

Уравнение реакции

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

N-bromosuccinimide

benzoyl peroxide

→

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

Выход 31.6%

Растворители

carbon tetrachloride

Условия реакции

Обработка

1. 1
   ДругоеNitrogen gas was bubbled through the mixture for 5 min
2. 2
   Температураthe resulting mixture was heated
3. 3
   Температураto reflux for 4 h
4. 4
   Другоеwas then placed in the refrigerator overnight
5. 5
   ДругоеThe solids formed
6. 6
   Другоеwere removed by filtration
7. 7
   Концентрированиеthe filtrate concentrated in vacuo
8. 8
   ДругоеThe crude product obtained
9. 9
   Другоеwas purified

Методика

To a stirred mixture of (E)-3-(3-bromo-phenoxy)-but-2-enoic acid ethyl ester (5.80 g, 0.020 mol) in carbon tetrachloride (30 mL) under a nitrogen atmosphere was added N-bromosuccinimide (5.51 g, 0.031 mol) and benzoyl peroxide (500 mg, 0.002 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-(3-bromo-phenoxy)-but-2-enoic acid ethyl ester (2.30 g, 31%) as a yellow oil.

Источник