P-Xylene → (Chloromethyl)(2,5-dimethylphenyl)(phenyl) sulfonium triflate

HRID 926957Notes

Reaction equation

HRID 926957 reaction equation
[C:1]1([S:7]([CH2:9][Cl:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1.[F:19][C:20]([F:33])([F:32])[S:21]([O:24]S(C(F)(F)F)(=O)=O)(=[O:23])=[O:22]>C(OCC)C>[O-:24][S:21]([C:20]([F:33])([F:32])[F:19])(=[O:23])=[O:22].[Cl:10][CH2:9][S+:7]([C:17]1[CH:16]=[C:15]([CH3:18])[CH:14]=[CH:13][C:12]=1[CH3:11])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7809P-XyleneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81624Chloromethyl phenyl sulfoxide

Product 1

HCID 131735039(Chloromethyl)(2,5-dimethylphenyl)(phenyl) sulfonium triflate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chloromethyl phenyl sulfoxide (300 mg, 1.94 mmol) of example 21 was dissolved in dry diethyl ether (7.5 mL) under an argon atmosphere. p-Xylene (227 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 (0.326 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred until the reaction was complete. The precipitate triflate salt formed was isolated by filtration and washed with cold diethyl ether at 0° C. 602 mg (75%) of the desired product was obtained as a oily solid after heating at room temperature.

Workup

  1. temperaturethe mixture was cooled to a temperature below −60° C
  2. additionwas added slowly
  3. temperaturemaintaining the same temperature

Sources & evidence

ORD record
ord-28ac372385f24babb758a18e9639e5cd
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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