Methanol → HCID 87870770, compound

HRID 1351062Notes

Reaction equation

HRID 1351062 reaction equation
[F:1][C:2]([F:8])(F)[S:3]([O-:6])(=[O:5])=[O:4].[CH:9]1([S:15][C:16]2[CH:21]=[CH:20][C:19]([S+:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[F:35][C:36]([F:42])(F)S([O-])(=O)=O.ClCl.[CH3:45]O>>[CH:29]12[CH2:45][CH:32]([CH2:31][CH2:30]1)[CH2:33][CH:34]2[C:36]([F:42])([F:35])[C:2]([F:8])([F:1])[S:3]([O-:6])(=[O:5])=[O:4].[CH:9]1([S:15][C:16]2[CH:21]=[CH:20][C:19]([S+:22]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 4

HCID 887MethanolHCID 24526ChlorineHCID 2758875TrifluoromethanesulfonateHCID 21097647HCID 21097647, compound

Product 1

HCID 87870770HCID 87870770, compound

Procedure

19.2 g of the resulting 4-cyclohexylthiophenyl diphenylsulfonium trifluoromethane sulfonate was dissolved in 100 g of methanol in a reaction flask. The mixture was fed into an ion-exchange chromatography (an ion-exchange resin: Shephadex R-QAE A-25, packing amount: 60 g, manufactured by Aldrich Corporation) to replace trifluoromethanesulfonate anions with chlorine ions. After evaporating methanol using an evaporator, the resulting residue was dissolved in 100 g of dichloromethane. 15 g of 30 wt % 2-(bicyclo[2.2.1]heptan-2-yl)-1,1,2,2-tetrafluoroethane sodium sulfonate aqueous solution was added. The mixture was stirred for one hour at room temperature and transferred to a separatory funnel, shaken, and allowed to stand still. The water layer was removed. 100 ml of distilled water was added and the mixture was shaken again and allowed to stand still. The water layer was removed. The resulting dichloromethane solution was dried with anhydrous magnesium sulfate and filtered. After evaporating dichloromethane from the dried solution, the residual liquid was dried under reduced pressure to obtain 20.1 g of 4-cyclohexylthiophenyl diphenylsulfonium 2-(bicyclo[2.2.1]heptan-2-yl)-1,1,2,2-tetrafluoroethanesulfonate.

Workup

  1. customAfter evaporating methanol using
  2. customan evaporator
  3. dissolutionthe resulting residue was dissolved in 100 g of dichloromethane
  4. addition15 g of 30 wt % 2-(bicyclo[2.2.1]heptan-2-yl)-1,1,2,2-tetrafluoroethane sodium sulfonate aqueous solution was added
  5. customtransferred to a separatory funnel
  6. stirringshaken
  7. customThe water layer was removed
  8. addition100 ml of distilled water was added
  9. stirringthe mixture was shaken again
  10. customThe water layer was removed
  11. dry with materialThe resulting dichloromethane solution was dried with anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customAfter evaporating dichloromethane from the dried solution
  14. customthe residual liquid was dried under reduced pressure

Sources & evidence

ORD record
ord-79bc40dc1a2d4daab8d9636476dd09e1
Source dataset
uspto-grants-2007_05
Patent number
US07217492B2

Reaction notes

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