Fluorine → 1-Fluoro-5-(trifluoromethyl)pyridin-1-ium-2-sulfonate

HRID 1492717Notes

Reaction equation

HRID 1492717 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[N:7][CH:8]=1.[F:15]F>C(#N)C>[F:15][N+:7]1[CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=[CH:5][C:6]=1[S:9]([O-:12])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 24524Fluorine2×HCID 107517625-(trifluoromethyl)pyridine-2-sulfonic Acid

Product 1

HCID 27376181-Fluoro-5-(trifluoromethyl)pyridin-1-ium-2-sulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 5-(trifluoromethyl)pyridine-2-sulfonic acid (227 mg, 1 mmol) and acetonitrile (60 ml) in a flask on a cooling bath kept at -10° C., a mixed gas of 10% fluorine/90% nitrogen was introduced at a flow rate of 15 ml/min. The total amount of the fluorine gas was 3.1 mmol. Thereafter, the nitrogen gas alone was introduced for 30 minutes. After the reaction mixture was concentrated, ethyl acetate was added to the residue. The precipitated crystal was recovered by filtration to obtain N-fluoro-5-(trifluoromethyl)pyridinium-2-sulfonate (212 mg, 0.86 mmol). Yield, 86%. Melting point, 190°-220° C. (with decomposition).

Workup

  1. customkept at -10° C.
  2. additionThereafter, the nitrogen gas alone was introduced for 30 minutes
  3. concentrationAfter the reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. filtrationThe precipitated crystal was recovered by filtration

Sources & evidence

ORD record
ord-29349e42304441cc8398b6247c2a29db
Source dataset
uspto-grants-1994_12
Patent number
US05374732

Reaction notes

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