Alpha-Methylstyrene → (3-bromoprop-1-en-2-yl)benzene

HRID 1639488Notes

Reaction equation

HRID 1639488 reaction equation
[C:1]1([C:7]([CH3:9])=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:10]N1C(=O)CCC1=O.BrC1C=CC=CC=1>>[Br:10][CH2:8][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:9]

Participants

4

Reactant 3

HCID 7407Alpha-MethylstyreneHCID 7961BromobenzeneHCID 67184N-bromobutanimide2×

Product 1

HCID 234998(3-bromoprop-1-en-2-yl)benzeneYield 46.2%

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.

Workup

  1. dissolutionwas dissolved
  2. customthe precipitate was subsequently removed by filtration
  3. washwashed with chloroform
  4. distillationThe filtrate was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-764b28f41ebf4e6b93d8e18d62a52a39
Source dataset
uspto-grants-2012_02
Patent number
US08110519B2

Reaction notes

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