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

HRID 926955Notes

Reaction equation

HRID 926955 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:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[C:13]=1[CH3:20].[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].[Cl:10][CH2:9][S+:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:17]1[CH:16]=[C:15]([CH3:18])[C:14]([CH3:19])=[C:13]([CH3:20])[C:12]=1[CH3:11]

Participants

5

Reactant 3

HCID 102631,2,3,4-TetramethylbenzeneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81624Chloromethyl phenyl sulfoxide

Product 1

HCID 87429243(Chloromethyl)(phenyl)(2,3,4,5-tetramethylphenyl)sulfonium triflate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chloromethyl phenyl sulfoxide (12 g, 68.71 mmol) of example 21 was dissolved in dry diethyl ether (100 mL) under an argon atmosphere. 1,2,3,4-Tetramethylbenzene (10.3 mL, 1 eq) was 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 (11.5 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 diethyl ether at 0° C. (50 mL). 16.18 g (57.4%) of the desired product was obtained as a white solid. mp: 125-127° C.

Workup

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

Sources & evidence

ORD record
ord-1242bfa3c511442181fb538b545c4746
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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