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

HRID 2377565Notes

Reaction equation

HRID 2377565 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 heated in a 160° C. oil bath until the N-bromosuccinimide dissolved. The reaction mixture was allowed to cool to room temperature. The precipitate was subsequently removed using filtration and was washed using chloroform. The filtrate was distilled under reduced pressure to purify it (b.p. 80° C. to 85° C./3 mmHg), and 3-bromo-2-phenylpropene (12.1 g) was obtained. 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. dissolutiondissolved
  2. customThe precipitate was subsequently removed
  3. filtrationfiltration
  4. washwas washed
  5. distillationThe filtrate was distilled under reduced pressure
  6. customto purify it (b.p. 80° C. to 85° C./3 mmHg)

Sources & evidence

ORD record
ord-aa8340cfaf99457694d363215e9ab211
Source dataset
uspto-grants-2008_12
Patent number
US07470646B2

Reaction notes

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