Pyridine → Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)

HRID 1440171Notes

Reaction equation

ClC(Cl)(Cl)F.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[F:12]F.[F:14][C:15]([F:21])([F:20])[S:16]([O-:19])(=[O:18])=[O:17].[Na+]>C(#N)C>[F:14][C:15]([F:21])([F:20])[S:16]([O-:19])(=[O:18])=[O:17].[F:12][N+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To a 50 ml trichlorofluoromethane solution containing 1.0 g (12.6 m moles) of pyridine a mixed gas of fluorine and nitrogen in a volumetric ratio of 1:9 was introduced at a rate of 30 ml/min. at -78° C. under vigorous stirring. The amount of the fluorine gas introduced amounted to 34.8 mmoles. Subsequent to the fluorine introduction, 20 ml of anhydrous acetonitrile and 2.2 g (12.8 mmoles) of sodium trifluoro-methanesulfonate as a XM reactant were added to the reaction solution after which the temperature of the solution was raised to -40° C., while removing the solvent with the aid of an aspirator. The solvent, after filtering sodium fluoride formed as a byproduct, was distilled off and the resultant residue was recrystallized from THF to give 1.75 g (yield: 67%) of N-fluoropyridinium trifluoromethanesulfonate, the physical properties of which are shown in Table 6.

Workup

additionwas introduced at a rate of 30 ml/min. at -78° C. under vigorous stirring
customwhile removing the solvent with the aid of an aspirator
filtrationThe solvent, after filtering sodium fluoride
customformed as a byproduct
distillationwas distilled off
customthe resultant residue was recrystallized from THF

Sources & evidence

ORD record: ord-304a2f2fa32746b185593f50b81bda92
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE035177

Reaction notes

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