p-Toluenesulfonic acid → HCID 22252737, compound

HRID 22992Notes

Reaction equation

HRID 22992 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:12][C:11]1([CH3:13])[C:4]2[C:3](=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)[S:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 106348752-Bromo-1-(3-methylbut-2-enylthio)benzene

Product 1

HCID 22252737HCID 22252737, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

26.00 g (102.0 mmol) of 2-bromo-1-(3-methylbut-2-enylthio)benzene, 130 ml of toluene and 23.20 g (122.0 mmol) of para-toluenesulphonic acid are introduced into a three-necked flask. The reaction mixture is heated at reflux for four hours and is evaporated to dryness. The residue is taken up in an aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column eluted with heptane. 20.00 g (76%) of the expected compound are collected in the form of an orangey oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for four hours
  3. customis evaporated to dryness
  4. extractionextracted with ethyl acetate
  5. customthe organic phase is separated
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a silica column
  10. washeluted with heptane
  11. custom20.00 g (76%) of the expected compound are collected in the form of an orangey oil

Sources & evidence

ORD record
ord-e085397cc5d5450497a7d3d8009c06a4
Source dataset
uspto-grants-2005_02
Patent number
US06849658B2

Reaction notes

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