Hexane → Sulfonium, triphenyl-, 1,1,1-trifluoromethanesulfonate (1:1)

HRID 584038Notes

Reaction equation

HRID 584038 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:28][C:29]([F:35])([F:34])[S:30]([OH:33])(=[O:32])=[O:31].[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C1C=CC=CC=1>[F:28][C:29]([F:35])([F:34])[S:30]([O-:33])(=[O:32])=[O:31].[C:1]1([S+:7]([C:38]2[CH:37]=[CH:36][CH:41]=[CH:40][CH:39]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 9845Trifluoroacetic anhydrideHCID 13679Diphenyl sulfoxideHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 11729320Sulfonium, triphenyl-, 1,1,1-trifluoromethanesulfonate (1:1)Yield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 200 ml of benzene were dissolved 21.1 g (0.1 mol) of diphenylsulfoxide, and 42.0 g (0.2 mol) of trifluoroacetic acid anhydride were added dropwise thereto at 0 to 5° C., followed by stirring and stirred at 0 to 5° C. for 30 minutes. And then, 15.0 g (0.1 mol) of trifluoromethane sulfonic acid were added dropwise thereto at 0 to 5° C. and allowed to react with stirring at 0 to 20° C. for 3 hours. After completion of the reaction, 500 ml of n-hexane was poured into the resultant and the obtained oily substance separated by decantation was crystallized from methylene chloride/n-hexane, followed by filtration and drying, to give 37.9 g (yield: 92%) of triphenylsulfonium trifluoromethanesulfonate as a white crystal.

Workup

  1. additionwere added dropwise
  2. customat 0 to 5° C.
  3. stirringstirred at 0 to 5° C. for 30 minutes
  4. customat 0 to 5° C.
  5. customto react
  6. stirringwith stirring at 0 to 20° C. for 3 hours
  7. additionwas poured into the resultant
  8. customthe obtained oily substance separated by decantation
  9. customwas crystallized from methylene chloride/n-hexane
  10. filtrationfollowed by filtration
  11. customdrying

Sources & evidence

ORD record
ord-76ad00ee7d6644eead5077931a8520a5
Source dataset
uspto-grants-2005_08
Patent number
US06924323B2

Reaction notes

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