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

HRID 982501Notes

Reaction equation

HRID 982501 reaction equation
C(#N)C.[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:10][C:11]([F:21])([F:20])[S:12]([O:15][Si](C)(C)C)(=[O:14])=[O:13].[F:22]F>CCOCC>[F:10][C:11]([F:21])([F:20])[S:12]([O-:15])(=[O:14])=[O:13].[F:22][N+:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 24524Fluorine2×HCID 65367Trimethylsilyl triflate

Product 1

HCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)Yield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 5 ml anhydrous acetonitrile solution containing 0.408 g (5.17 mmoles) of pyridine, 1.0 ml (5.17 mmoles) of trimethylsilyl trifluoromethanesulfonate as the XM reactant was added at -40° C. under stirring. To the resultant solution a mixed gas of fluorine and nitrogen (1:9), 10 minutes after the addition, was introduced at a rate of 15 ml/min. The amount of fluorine gas introduced was 15.5 mmoles. After the completion of the reaction, an amount of ether cooled to -60° C. was added to the solution to precipitate crystals which were filtered to give 0.99 g (yield: 78%) of N-fluoropyridinium trifluoromethanesulfonate.

Workup

  1. additionwas added at -40° C.
  2. additionwas introduced at a rate of 15 ml/min
  3. customAfter the completion of the reaction
  4. additionwas added to the solution
  5. customto precipitate crystals which
  6. filtrationwere filtered

Sources & evidence

ORD record
ord-748527fc22ee4110aa6367d0841f543a
Source dataset
uspto-grants-1991_02
Patent number
US04996320

Reaction notes

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