1,2,3,4-Tetramethylbenzene → (Fluoromethyl)(2,3,4,5-tetramethylphenyl)(p-tolyl)sulfonium triflate
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:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[C:14]=1[CH3:21].[F:22][C:23]([F:36])([F:35])[S:24]([O:27]S(C(F)(F)F)(=O)=O)(=[O:26])=[O:25]>C(OCC)C>[O-:27][S:24]([C:23]([F:36])([F:35])[F:22])(=[O:26])=[O:25].[F:1][CH2:2][S+:3]([C:18]1[CH:17]=[C:16]([CH3:19])[C:15]([CH3:20])=[C:14]([CH3:21])[C:13]=1[CH3:12])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1Participants
Procedure
1-((Fluoromethyl)sulfinyl)-4-methylbenzene (3 g, 17.42 mmol) of example 5 was dissolved in dry diethyl ether (100 ml) under nitrogen atmosphere. 1,2,3,4-Tetramethylbenzene (2.60 mL, 1.0 eq) was added to the previous solution and then the mixture was cooled to a temperature below −10° C. Trifluoromethanesulfonic anhydride (2.93 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred at the same temperature, until the reaction was complete. A pink suspension was formed and after 3 hours, turned into a light grey suspension. The precipitate triflate salt was isolated by filtration, washed with diethyl ether at 0° C. and dried under vacuum at a temperature below 30° C. 5.68 g (79.44%) of the desired product was obtained as a white solid.
Workup
- temperaturethe mixture was cooled to a temperature below −10° C
- temperaturemaintaining the same temperature
- customA pink suspension was formed and after 3 hours
Sources & evidence
- ORD record
- ord-0d4075e4d55842a08285a1a1bb10fae1
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290446B2
Reaction notes
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