Benzene → S-(trifluoromethyl)phenyl-2-trifluoromethylthiophenylsulfonium Triflate
Reaction equation
[O:1]([S:9]([C:12]([F:15])([F:14])[F:13])(=O)=O)[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[O-:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[F:6][C:5]([F:8])([F:7])[S+:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:9][C:12]([F:13])([F:14])[F:15]Participants
3
Procedure
S-(trifluoromethyl)phenyl-2-trifluoromethylthiophenylsulfonium triflate (17) was synthesized as shown in FIG. 11. 1,2-Diiodobenzene was converted to phenyl 1,2-bis(trifluoromethyl sulfide) (14) in 84% yield. Compound 14 was oxidized to phenyl 1,2-bis(trifluoromethyl sulfoxide) (15) under reflux. No sulfone was isolated with the only by-product being phenyl 2-trifluoromethylthio trifluoromethyl sulfoxide (16). It is likely that a bulk steric effect hindered further oxidation and the reaction stopped at the sulfoxide stage. Compound 15 reacted with benzene and Tf2O to give the product S-(trifluoromethyl)phenyl-2-trifluoromethylthiophenylsulfonium triflate (17).
Sources & evidence
- ORD record
- ord-62a6ace6de3b4f6b80aac36bc070e55c
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06215021B1
Reaction notes
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