Nitric Acid → 2,7-dinitro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate

HRID 974075Notes

Reaction equation

HRID 974075 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[N+:16]([O-:19])([OH:18])=O.[O:20]=[N+:21]=[O:22].FC(F)(F)S([O-])(=O)=O.[F:31][C:32]([F:47])([F:46])[S+:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[C:35]2[CH:42]=[CH:43][CH:44]=[CH:45][C:34]1=2>C(OCC)C>[F:1][C:2]([F:15])([F:14])[S:3]([O-:6])(=[O:5])=[O:4].[N+:16]([C:43]1[CH:44]=[CH:45][C:34]2[S+:33]([C:32]([F:46])([F:31])[F:47])[C:37]3[CH:38]=[C:39]([N+:21]([O-:22])=[O:20])[CH:40]=[CH:41][C:36]=3[C:35]=2[CH:42]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 67749Trifluoromethanesulfonic anhydrideHCID 27775075-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonateHCID 3609161Nitronium

Product 1

HCID 446307722,7-dinitro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonateYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trifluoromethanesulfonic anhydride 4.57 ml (27.2 mmol) was added to 0.94 ml (22.4 mmol) of 94% nitric acid and the mixture was stirred at room temperature for 1 hour to prepare nitronium trfluoromethanesulfonate. S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate 3.0 g (7.46 mmol) was added to the mixture and the reaction mixture was stirred for 2 day. Pale yellow crystals formed by addition of diethyl ether were collected by filtration and recrystallized from acetonitrile-diethyl ether to give 2.57 g (70%) of 2,7-dinitro-S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate. The properties of the product are summarized in Table 1.

Workup

  1. stirringthe reaction mixture was stirred for 2 day
  2. filtrationwere collected by filtration
  3. customrecrystallized from acetonitrile-diethyl ether

Sources & evidence

ORD record
ord-811d6782fdc745839dce8f09622dbd58
Source dataset
uspto-grants-1991_11
Patent number
US05066795

Reaction notes

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