HCID 18411305, compound → HCID 23133152, compound

HRID 2284889Notes

Reaction equation

HRID 2284889 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([S+:16]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.[S:30]([C:34]([C:37]([C:40]([C:43]([F:46])([F:45])[F:44])([F:42])[F:41])([F:39])[F:38])([F:36])[F:35])([O-:33])(=[O:32])=[O:31].[K+]>O>[S:30]([C:34]([C:37]([C:40]([C:43]([F:44])([F:45])[F:46])([F:41])[F:42])([F:39])[F:38])([F:36])[F:35])([O-:33])(=[O:32])=[O:31].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([S+:16]([C:23]2[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 18411305HCID 18411305, compoundHCID 23675274Potassium perfluorobutanesulfonate

Product 1

HCID 23133152HCID 23133152, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Bis(4-hydroxyphenyl)phenylsulfonium triflate (2.5 g, 0.00739 moles; Dainippon Pharmaceuticals) was dissolved in 20 mL of water in a suitable container to which was added potassium nonaflate (3.28 g, 0.00739 mole). To this mixture was added 120 mL of water, which formed a cloudy solution. This solution was stirred overnight at room temperature in a stoppered flask. The formed oil was separated from the aqueous layer by decanting this layer away. The residual oil was washed with 2 mL of distilled water. This residue was dissolved in 4 mL acetone and another 2.6 g of potassium nonaflate and 100 mL of water. This mixture was then extracted with 100 mL of methylene chloride after stirring overnight. The methylene chloride layer was washed with water several times and stripped of solvents. Dissolving in a minimum of methylene chloride the residue was precipitated with pentane and then dried under high vacuum to give 2.68 g of white solid (61% yield) which was pure by 1H and 19F NMR.

Workup

  1. customformed a cloudy solution
  2. customThe formed oil was separated from the aqueous layer
  3. customby decanting this layer away
  4. washThe residual oil was washed with 2 mL of distilled water
  5. dissolutionThis residue was dissolved in 4 mL acetone
  6. extractionThis mixture was then extracted with 100 mL of methylene chloride
  7. stirringafter stirring overnight
  8. washThe methylene chloride layer was washed with water several times
  9. dissolutionDissolving in a minimum of methylene chloride the residue
  10. customwas precipitated with pentane
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-4aa2ea724f1747b49871c6a86283b97d
Source dataset
uspto-grants-2015_09
Patent number
US09146467B2

Reaction notes

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