p-Toluenesulfonic acid → 7-Bromo-4,4-dimethylthiochroman

HRID 858270Notes

Reaction equation

HRID 858270 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])(=O)=O)[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:3]=[C:4]2[C:5]([C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][S:8]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18768217HCID 18768217, compound

Product 1

HCID 223930997-Bromo-4,4-dimethylthiochromanYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25.00 g (97.0 mmol) of 1-bromo-3-(3-methylbut-2-enylsulphonyl)benzene, 200 ml of toluene and 27.75 g (146.0 mmol) of para-toluenesulphonic acid are introduced into a three-necked flask. The reaction medium is refluxed for four hours and evaporated to dryness. The residue is taken up in aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with heptane. 22.57 g (90%) of the expected compound are obtained in the form of a yellow oil.

Workup

  1. temperatureThe reaction medium is refluxed for four hours
  2. customevaporated to dryness
  3. extractionextracted with ethyl acetate
  4. customthe organic phase is separated out after settling
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with heptane

Sources & evidence

ORD record
ord-ef75afe850a246058183ba50cc54a66d
Source dataset
uspto-grants-2006_12
Patent number
US07148245B2

Reaction notes

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