Réaction #1726670

Équation de réaction

N-bromosuccinimide

2-phenylpropene

N-bromosuccinimide

bromobenzene

→

3-bromo-2-phenylpropene

Rendement 46.2%

Conditions de réaction

Traitement

1. 1
   workup.DISSOLUTIONwas dissolved
2. 2
   Autrethe precipitate was subsequently removed by filtration
3. 3
   Lavagewashed with chloroform
4. 4
   workup.DISTILLATIONThe filtrate was purified by distillation under reduced pressure

Mode opératoire

A mixture of 2-phenylpropene (22.4 g, 190 mmoles), N-bromosuccinimide (23.7 g, 133 mmoles) and bromobenzene (76 ml) was superheated on an oil bath at 160° C. until the N-bromosuccinimide was dissolved. The reaction mixture was cooled to room temperature, and the precipitate was subsequently removed by filtration and washed with chloroform. The filtrate was purified by distillation under reduced pressure to obtain 12.1 g of 3-bromo-2-phenylpropene (b.p. 80° C. to 85° C./3 mmHg). 1H-NMR (CDCl3)δ=4.39 (s, 2H), 5.49 (s, 1H), 5.56 (s, 1H), 7.33-7.51 (m, 5H); 13C NMR (CDCl3)δ=34.2, 117.2, 126.1, 128.3, 128.5, 137.6, 144.2.

Source