Tert-Butylbenzene → (4-(Tert-butyl)phenyl)(chloromethyl)(phenyl)sulfonium triflate

HRID 2199390Notes

Reaction equation

HRID 2199390 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]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[F:21][C:22]([F:35])([F:34])[S:23]([O:26]S(C(F)(F)F)(=O)=O)(=[O:25])=[O:24]>C(OCC)C>[O-:26][S:23]([C:22]([F:35])([F:34])[F:21])(=[O:25])=[O:24].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S+:7]([CH2:9][Cl:10])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81624Chloromethyl phenyl sulfoxide

Product 1

HCID 86699376(4-(Tert-butyl)phenyl)(chloromethyl)(phenyl)sulfonium triflate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chloromethyl phenyl sulfoxide (200 mg, 1.29 mmol) of example 21 was dissolved in dry diethyl ether (7.5 mL) under an argon atmosphere. tert-Butyl benzene (0.191 g, 1.1 eq) was added to the previous solution and then the mixture was cooled to a temperature below −60° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.217 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 0.487 g as red 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 0.487 g as red viscous oil

Sources & evidence

ORD record
ord-cb5d240bbcea4662ad75e6a1db711fce
Source dataset
uspto-grants-2016_06
Patent number
US09359294B2

Reaction notes

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