Cumene → (Fluoromethyl)(isopropylphenyl)(p-tolyl)sulfonium tetrafluoroborate
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.[C:12]1([CH:18]([CH3:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[H+].[B-:37]([F:41])([F:40])([F:39])[F:38]>C(OCC)C>[F:38][B-:37]([F:41])([F:40])[F:39].[F:1][CH2:2][S+:3]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:18]([CH3:20])[CH3:19])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1-((Fluoromethyl)sulfinyl)-4-methylbenzene (738 mg, 4.29 mmol) of example 5 was dissolved in dry diethyl ether (15 mL) under an argon atmosphere. Cumene (0.66 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 (0.72 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred, at the same temperature, until the reaction was complete. HBF4 in diethyl ether solution (54%, 1.18 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 a slightly yellow oily solid (2.22 g) after heating at room temperature.
Workup
- temperaturethe mixture was cooled to a temperature below −50° C
- additionwas added slowly
- temperaturemaintaining the same temperature
- stirringThe resulting suspension was stirred for 30 minutes
Sources & evidence
- ORD record
- ord-4f51eb4394aa4546a92227ec76c76c20
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290446B2
Reaction notes
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