Nitric Acid → 2-nitro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]([F:19])([F:18])[S:7]([O:10]S(C(F)(F)F)(=O)=O)(=[O:9])=[O:8].FC(F)(F)S([O-])(=O)=O.O=[N+]=O.FC(F)(F)S([O-])(=O)=O.[F:39][C:40]([F:55])([F:54])[S+:41]1[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[C:43]2[CH:50]=[CH:51][CH:52]=[CH:53][C:42]1=2>[N+](C)([O-])=O>[F:5][C:6]([F:19])([F:18])[S:7]([O-:10])(=[O:9])=[O:8].[N+:1]([C:51]1[CH:52]=[CH:53][C:42]2[S+:41]([C:40]([F:54])([F:39])[F:55])[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=3[C:43]=2[CH:50]=1)([O-:4])=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 0.058 ml (1.3 mmol) of 94% nitric acid and 0.266 ml (1.58 mmol) of trifluoromethanesulfonic anhydride was stirred at room temperature for 1.5 hours to prepare nitronium trifluoromethanesulfonate, and then 2 ml of nitromethane and 502 mg (1 mmol) of S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate was added to the mixture. The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure. Diethyl ether was added to the residue and the resulting precipitate was collected by filtration to give 339 mg (76%) of 2-nitro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate as pale yellow crystals. The properties of the product are summarized in Table 1.
Workup
- stirringThe reaction mixture was stirred overnight at room temperature
- concentrationconcentrated under reduced pressure
- additionDiethyl ether was added to the residue
- filtrationthe resulting precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-580f061aba05415f9600b14a33a645d4
- Source dataset
- uspto-grants-1991_11
- Patent number
- US05066795
Reaction notes
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