O-Xylene → (3,4-Dimethylphenyl)(fluoromethyl)(phenyl)sulfonium tetrafluoroborate

HRID 926944Notes

Reaction equation

HRID 926944 reaction equation
[C:1]1([S:7]([CH2:9][F:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[CH3:18].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[H+].[B-:35]([F:39])([F:38])([F:37])[F:36]>C(OCC)C>[F:36][B-:35]([F:39])([F:38])[F:37].[CH3:11][C:12]1[CH:13]=[C:14]([S+:7]([CH2:9][F:10])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=[CH:16][C:17]=1[CH3:18]

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 28118Tetrafluoroboric acidHCID 67749Trifluoromethanesulfonic anhydrideHCID 325133(Fluoromethanesulfinyl)benzene

Product 1

HCID 87429276(3,4-Dimethylphenyl)(fluoromethyl)(phenyl)sulfonium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Monofluoromethyl phenyl sulfoxide (645 mg, 4.08 mmol) of example 2 was dissolved in dry diethyl ether (15 ml) under argon atmosphere. O-xylene (0.54 ml, 1.1 eq) was added to the previous solution and then the mixture was cooled to a temperature below −50° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.68 mL, 1.0 eq) was added slowly maintaining the same temperature. The mixture was stirred until the reaction was complete. HBF4 solution (54%, 1.12 mL, 2 eq) was added and the resulting suspension was stirred for 30 minutes. The precipitate tetrafluoroborate salt was isolated by filtration, washed with diethyl ether at 0° C. and dried. The desired product was obtained as a slightly yellow oily solid (1.729 g).

Workup

  1. temperaturethe mixture was cooled to a temperature below −50° C
  2. additionwas added slowly
  3. temperaturemaintaining the same temperature
  4. stirringthe resulting suspension was stirred for 30 minutes

Sources & evidence

ORD record
ord-3953578faeab45d8a862d64455a4b1aa
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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