Trifluoromethanesulfonic anhydride → Trifluoromethanesulfonic anhydride

HRID 1795309Notes

Reaction equation

HRID 1795309 reaction equation
[Li]C(C)(C)C.[O:6]([S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])[S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8].C([C:25]1[C:30]([F:31])=[C:29]([F:32])[C:28]([CH:33]([S:41]([C:44]([F:47])([F:46])[F:45])(=[O:43])=[O:42])[S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[C:27]([F:48])[C:26]=1[F:49])(C)(C)C>>[F:48][C:27]1[C:28]([CH:33]([S:41]([C:44]([F:45])([F:46])[F:47])(=[O:42])=[O:43])[S:34]([C:37]([F:39])([F:40])[F:38])(=[O:35])=[O:36])=[C:29]([F:32])[C:30]([F:31])=[C:25]([F:11])[C:26]=1[F:49].[O:6]([S:7]([C:10]([F:13])([F:11])[F:12])(=[O:9])=[O:8])[S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 23237351HCID 23237351, compoundHCID 178418306HCID 178418306, compound

Product 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 102039861-[Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene

Procedure

As it is described in Table 2 that the yield of pentafluorophenylbis(triflyl)methane is 45%, it was revealed that when pentafluorophenylbis(triflyl)methane is produced using a pentafluorophenylmethyl triflone, both of pentafluorophenylbis(triflyl)methane and 4-tert-butyl-2,3,5,6-tetrafluorophenylbis(triflyl)methane can be obtained at a ratio of 1:1 (45% yield, respectively). However, it was found out that when 1.0 equivalent weight of t-BuLi and 0.5 equivalent weight of Tf2O are used, the production of 4-tert-butyl-2,3,5,6-tetrafluorophenylbis(triflyl)methane is completely suppressed, and pentafluorophenylbis(triflyl)methane can be obtained at 95% yield with Tf2O as a base. Consequently, the reactions of pentafluorophenylbis(triflyl)methane with the various types of alkyl lithium reagents were examined, in order to determine the generality and range of the nucleophilic substitution specific to the para position of pentafluorophenylbis(triflyl)methane. Table 3 shows the types of alkyl lithium reagents, the reaction conditions and the yield of the para position substituents of pentafluorophenylbis(triflyl)methane. The para position substituents of pentafluorophenylbis(triflyl)methane shown in Table 3 are obtained by washing the reaction product obtained by reacting pentafluorophenylbis(triflyl)methane with alkyl lithium reagent, with a hydrochloric solution. The “Bn” shown in Table 3 represents a benzyl group.

Sources & evidence

ORD record
ord-39e72390c93a4ecc9ca9956b6852a1d5
Source dataset
uspto-grants-2006_04
Patent number
US07026409B2

Reaction notes

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