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

HRID 926965Notes

Reaction equation

HRID 926965 reaction equation
[C:1]1([S:7]([CH2:9][Br: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].[Br: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 11816834Bromomethyl phenyl sulfoxide

Product 1

HCID 87429207(Bromomethyl)(phenyl)(2,3,4,5-tetramethylphenyl)sulfonium triflate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromomethyl phenyl sulfoxide (500 mg, 2.29 mmol) of example 32 was dissolved in dry diethyl ether (15 mL) under an argon atmosphere. 1,2,3,4-Tetramethylbenzene (339 mg, 1.09 eq) was added to the previous solution and then the mixture cooled to a temperature below −60° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.385 ml, 1.0 eq) was added slowly, maintaining the same temperature. The mixture was stirred until the reaction was complete. The precipitated triflate salt formed was isolated by filtration, washed with diethyl ether at 0° C. and dried under vacuum. 0.779 g (70%) of the desired product was obtained as a white solid. mp: 115-116° C.

Workup

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

Sources & evidence

ORD record
ord-c35f29e2cac34eba877b0f75ee92aed9
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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