1,2,3,4-Tetramethylbenzene → (Chloromethyl)(2,3,4,5-tetramethylphenyl)(p-tolyl)sulfonium triflate

HRID 2199393Notes

Reaction equation

HRID 2199393 reaction equation
[Cl:1][CH2:2][S:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[C:14]=1[CH3:21].[F:22][C:23]([F:36])([F:35])[S:24]([O:27]S(C(F)(F)F)(=O)=O)(=[O:26])=[O:25]>C(OCC)C>[O-:27][S:24]([C:23]([F:36])([F:35])[F:22])(=[O:26])=[O:25].[Cl:1][CH2:2][S+:3]([C:18]1[CH:17]=[C:16]([CH3:19])[C:15]([CH3:20])=[C:14]([CH3:21])[C:13]=1[CH3:12])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 102631,2,3,4-TetramethylbenzeneHCID 67749Trifluoromethanesulfonic anhydrideHCID 111270441-[(Chloromethyl)sulfinyl]-4-methylbenzene

Product 1

HCID 131735041(Chloromethyl)(2,3,4,5-tetramethylphenyl)(p-tolyl)sulfonium triflate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-((chloromethyl)sulfinyl)-4-methylbenzene (500 mg, 2.65 mmol) of example 29 was dissolved in dry diethyl ether (5 mL) under an argon atmosphere. 1,2,3,4-Tetramethylbenzene (0.40 mL, 1 eq) was slowly added to the previous solution and then the mixture was cooled to a temperature between 5° C. and 0° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.45 mL, 1 eq) was added maintaining the same temperature. The mixture was stirred until the reaction was complete. The precipitated triflate salt was isolated by filtration and washed with diethyl ether (5 mL) at 0° C. 1.12 g (89.74%) of the desired product was obtained as a white solid. Mp=28-30° C.

Workup

  1. temperaturethe mixture was cooled to a temperature between 5° C. and 0° C
  2. additionwas added
  3. temperaturemaintaining the same temperature

Sources & evidence

ORD record
ord-984105186cd74700975addee864213db
Source dataset
uspto-grants-2016_06
Patent number
US09359294B2

Reaction notes

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