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

HRID 2199380Notes

Reaction equation

HRID 2199380 reaction equation
[F: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:14]=[CH:15][CH:16]=[CH:17][C:18]=1[CH3:19].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[H+].[B-:36]([F:40])([F:39])([F:38])[F:37]>C(OCC)C>[F:37][B-:36]([F:40])([F:39])[F:38].[CH3:12][C:13]1[CH:14]=[C:15]([S+:3]([CH2:2][F:1])[C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=2)[CH:16]=[CH:17][C:18]=1[CH3:19]

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 28118Tetrafluoroboric acidHCID 67749Trifluoromethanesulfonic anhydrideHCID 3251341-(Fluoromethylsulfinyl)-4-methylbenzene

Product 1

HCID 87429327(3,4-Dimethylphenyl)(fluoromethyl)(p-tolyl)sulfonium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1-((Fluoromethyl)sulfinyl)-4-methylbenzene (576 mg, 3.34 mmol) of example 5 was dissolved in dry diethyl ether (15 mL) under argon atmosphere. O-Xylene (0.445 mL, 1.10 eq) was added to the previous solution. The mixture was cooled to a temperature below −50° C. After stabilizing the temperature below −50° C., trifluoromethanesulfonic anhydride (0.562 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred, until the reaction was complete. HBF4 in diethyl ether solution (54%, 0.921 mL, 2 eq) was added. The resulting suspension was stirred for 30 minutes. The precipitate tetrafluoroborate salt was isolated by filtration and washed with diethyl ether at 0° C. The desired product was obtained as an oily solid (1.42 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-0bae30c156934353b79febfe59bd7ede
Source dataset
uspto-grants-2016_06
Patent number
US09359294B2

Reaction notes

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