p-Toluenesulfonic acid monohydrate → 2-(5-Bromoindane-1-ylidene)-1,3-dithiane

HRID 2046552

Reaction equation

HRID 2046552 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]([CH:12]1[S:17][CH2:16][CH2:15][CH2:14][S:13]1)(O)[CH2:6][CH2:5]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:12]1[S:13][CH2:14][CH2:15][CH2:16][S:17]1)[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 574194845-bromo-1-(1,3-dithian-2-yl)-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 574194852-(5-Bromoindane-1-ylidene)-1,3-dithiane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (rac)-5-bromo-1-[1,3]dithian-2-yl-indan-1-ol (2.15 g, 6.49 mmol) and p-toluenesulfonic acid monohydrate (309 mg, 1.62 mmol) in benzene (30 ml) was heated to reflux for 2 h using a Dean-Stark trap to remove water. The brown solution was allowed to cool to room temperature and was diluted with sat. NaHCO3 solution. The layers were separated and the organic layer was washed with brine, dried with Na2SO4 and evaporated. The title compound was obtained as brown gum (2.024 g, 99%) and was used without purification for the next reaction step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customto remove water
  4. additionwas diluted with sat. NaHCO3 solution
  5. customThe layers were separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried with Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-074c5ef97fa1482094f2dbc5e672e221
Source dataset
uspto-grants-2013_11
Patent number
US08592426B2

Linked notes

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