Reaction #1726670

Reaction equation

N-bromosuccinimide

2-phenylpropene

N-bromosuccinimide

bromobenzene

→

3-bromo-2-phenylpropene

Yield 46.2%

Conditions

Workup

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

Procedure

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