p-Toluenesulfonic acid → 1-Bromo-4-cyclopentenylbenzene

HRID 2244310Notes

Reaction equation

HRID 2244310 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 231542891-(4-Bromophenyl)cyclopentan-1-ol

Product 1

HCID 115286721-Bromo-4-cyclopentenylbenzeneYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2.62 g of 1-(4-bromo-phenyl)-cyclopentanol (10.9 mmol) in 50 ml toluene were added 124 mg of toluene-4-sulfonic acid (1 mmol) and the mixture was heated to reflux for 4 h. After the reaction mixture was allowed to cool to RT it was washed with sat. NaHCO3-solution and brine, dried (MgSO4), filtered and concentrated in vacuo to give 2.12 g of 1-bromo-4-cyclopent-1-enyl-benzene (88%) as an off-white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. washwas washed with sat. NaHCO3-solution and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ae818e3ef54423996a958525ee00fae
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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