Fluorine → HCID 18951399, compound

HRID 1492716Notes

Reaction equation

HRID 1492716 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:4]([S:9]([OH:12])(=[O:11])=[O:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[F:15]F>C(#N)C>[F:15][N+:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:1])[F:14])[C:4]=1[S:9]([O-:12])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 24524Fluorine2×HCID 18951398HCID 18951398, compound

Product 1

HCID 18951399HCID 18951399, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(trifluoromethyl)pyridine-2-sulfonic acid (115 mg, 0.5 mmol) and acetonitrile (20 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 1.5 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-3-(trifluoromethyl)pyridinium-2-sulfonate (84.6 mg, 0.345 mmol). Yield, 69%. Melting point, 180°-196° 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-2c5c18885be7472cb586cc9a1f60b050
Source dataset
uspto-grants-1994_12
Patent number
US05374732

Reaction notes

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