Acetonitrile → 1-Fluoro-4,6-bis(trifluoromethyl)pyridin-1-ium-2-sulfonate

HRID 1492710Notes

Reaction equation

HRID 1492710 reaction equation
C(#N)C.[F:4][C:5]([F:21])([F:20])[C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]([S:16]([OH:19])(=[O:18])=[O:17])[CH:7]=1.[F:22]F>C(OCC)C>[F:22][N+:9]1[C:10]([C:12]([F:13])([F:15])[F:14])=[CH:11][C:6]([C:5]([F:4])([F:20])[F:21])=[CH:7][C:8]=1[S:16]([O-:19])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24524Fluorine2×HCID 10685264HCID 10685264, compound

Product 1

HCID 27372911-Fluoro-4,6-bis(trifluoromethyl)pyridin-1-ium-2-sulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 25 ml flask, acetonitrile (6 ml) was added to 4,6-bistrifluoromethylpyridine-2-sulfonic acid (874 mg, 2.64 mmol) to prepare a homogeneous mixture. Then, the flask was dipped in a cooling bath kept at -40° C., and to the mixture, the fluorine gas diluted with the nitrogen gas to a concentration of 10% was introduced at a flow rate of 15 ml/min. The total amount of the fluorine gas was 211 ml. As the fluorination reaction proceeded, a precipitate was formed. After the reaction, only the nitrogen gas was introduced for 30 minutes. After the addition of ethyl ether to the mixture, the resulting precipitate was recovered by filtration to obtain N-fluoro-4,6-bistrifluoromethylpyridinium-2-sulfonate (787 mg). Yield, 95%. Melting point, 172°-174° C. (with decomposition).

Workup

  1. customto prepare a homogeneous mixture
  2. customThen, the flask was dipped in a cooling bath
  3. customkept at -40° C.
  4. additionwas introduced at a flow rate of 15 ml/min
  5. customAs the fluorination reaction
  6. customa precipitate was formed
  7. customAfter the reaction
  8. additiononly the nitrogen gas was introduced for 30 minutes
  9. filtrationthe resulting precipitate was recovered by filtration

Sources & evidence

ORD record
ord-7b784b179a35487cb0dc1e662425932b
Source dataset
uspto-grants-1994_12
Patent number
US05374732

Reaction notes

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