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

HRID 1742057Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:7][C:8]([F:14])([F:13])[S:9]([OH:12])(=[O:11])=[O:10].[F:15]F>C(#N)C>[F:7][C:8]([F:14])([F:13])[S:9]([O-:12])(=[O:11])=[O:10].[F:15][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To 40 ml of acetonitrile as solvent were added 1.592 g (20.136 mmol) of pyridine and 2.940 9 (19.588 mmol) of trifluoromethanesulfonic acid (i.e., the amount of pyridine was 1.03 times that of trifluoromethanesulfonic acid in a molar ratio), and the mixture was cooled to -20° C. A mixed gas of fluorine and nitrogen in a volumetric ratio of 1:4 was then introduced to the mixture at a rate of 50 ml/min under stirring. The amount Of fluorine gas introduced was 40.0 mmol. Alter completion of the reaction, the solvent was distilled off, and 4.716 g (19,097 mmol) of N-fluoropyridinium trifluoromethanesulfonate was obtained by crystallizing with ether. The yield was 97.4%. Characteristics and spectrum data of the compound are shown as follows.

Workup

customcompletion of the reaction
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-8bfb6764cd8440df8fc7239cf0836781
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05336772

Reaction notes

Loading…