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

Temperature

-40 °C

To a 100 ml anhydrous acetonitrile solution containing 10 g (0.126 mole) of pyridine a mixed gas of fluorine and nitrogen was introduced at a rate of 90 ml/min. at -40° C. under vigorous stirring. The amount of the fluorine gas introduced amounted to 0.18 mole. Subsequent to the fluorine introduction, 22 g (0.128 mole) of sodium trifluoromethanesulfonate as a XM reactant was added to the reaction solution after which the resultant reaction solution was maintained at -40° C. for 5 hours under stirring. Subsequently, the solvent, after filtering sodium fluoride, was distilled off and the resultant residue was recrystallized from methylene chloride to give 17.5 g (yield: 71%) of N-fluoropyridinium trifluoromethanesulfonate. The product thus obtained was repurified with methylene chloride/acetonitrile to recover 13.8 g (yield: 56%).

1. additionwas introduced at a rate of 90 ml/min. at -40° C. under vigorous stirring
2. customreaction solution
3. filtrationSubsequently, the solvent, after filtering sodium fluoride
4. distillationwas distilled off
5. customthe resultant residue was recrystallized from methylene chloride

ORD record

ord-ac517d2fd18b4c019af87d160ed2dbba

Source dataset

uspto-grants-1991_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04996320