p-Toluenesulfonic acid → 4,4-Dimethyl-8-bromothiochroman

HRID 1612013Notes

Reaction equation

HRID 1612013 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 222527374,4-Dimethyl-8-bromothiochroman

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

26.00 g (102.0 mmol) of 2-bromo-1-(3-methylbut-2-enylthio)benzene, 180 ml of toluene and 23.20 g (122.0 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 by settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica, eluting with heptane. 20.00 g (76%) of the expected compound are collected in the form of an orange-coloured 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
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluting with heptane
  10. custom20.00 g (76%) of the expected compound are collected in the form of an orange-coloured oil

Sources & evidence

ORD record
ord-f929a3fd035343a4bf5bf897a32b7b67
Source dataset
uspto-grants-2006_01
Patent number
US06992094B1

Reaction notes

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