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

HRID 1871553Notes

Reaction equation

HRID 1871553 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 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-9ccbe0a8beb0474eb0377ebe08f558fb
Source dataset
uspto-grants-2000_08
Patent number
US06103762

Reaction notes

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