Cumene → (Chloromethyl)(isopropylphenyl)(phenyl)sulfonium triflate

HRID 926958Notes

Reaction equation

HRID 926958 reaction equation
[C:1]1([S:7]([CH2:9][Cl:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([CH:17]([CH3:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F:20][C:21]([F:34])([F:33])[S:22]([O:25]S(C(F)(F)F)(=O)=O)(=[O:24])=[O:23]>C(OCC)C>[O-:25][S:22]([C:21]([F:34])([F:33])[F:20])(=[O:24])=[O:23].[Cl:10][CH2:9][S+:7]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:17]([CH3:19])[CH3:18])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7406CumeneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81624Chloromethyl phenyl sulfoxide

Product 1

HCID 86699374(Chloromethyl)(isopropylphenyl)(phenyl)sulfonium triflate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chloromethyl phenyl sulfoxide (170 mg, 1.1 mmol) of example 21 was dissolved in dry diethyl ether (5 mL) under an argon atmosphere. Cumene (145 mg, 1.1 eq) was added to the previous solution and the mixture was cooled to a temperature below −60° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.184 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred until the reaction was complete. The orange precipitated triflate salt was quickly filtered at −60° C. affording 0.399 g as orange viscous oil after heating at room temperature, which was a mixture by proton NMR.

Workup

  1. temperaturethe mixture was cooled to a temperature below −60° C
  2. additionwas added slowly
  3. temperaturemaintaining the same temperature
  4. customThe orange precipitated triflate salt
  5. filtrationwas quickly filtered at −60° C.
  6. customaffording 0.399 g as orange viscous oil

Sources & evidence

ORD record
ord-7225fceb28cc423fa14a0d43ccb84cd2
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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