Sodium Fluoride → 1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate (Fluorinating Reagent)

HRID 982502Notes

Reaction equation

HRID 982502 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[B-:10]([F:14])([F:13])([F:12])[F:11].[Na+].[F-:16].[Na+].N#N.FF.FF>C(#N)C>[F:11][B-:10]([F:14])([F:13])[F:12].[F:16][N+:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]

Participants

7

Reactant 5

HCID 5235Sodium FluorideHCID 79532,4,6-TrimethylpyridineHCID 24524FluorineHCID 4343483Sodium TetrafluoroborateHCID 131710817Fluorine nitrogen

Product 1

HCID 27793091-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate (Fluorinating Reagent)Yield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 25 ml pear-shaped flask, 2,4,6-trimethylpyridine (1.21 g, 10 mmoles), sodium borofluoride (1.23 g, 10 mmoles) as the XM reactant and anhydrous sodium fluoride (2.1 g, 50 mmoles) were dissolved in 15 ml of anhydrous acetonitrile and to the resulting solution a mixed gas of nitrogen/fluorine (9:1) was introduced at a rate of 50 ml/min. at -40° C. under vigorous stirring. The amount of fluorine introduced was 20 mmoles. After the completion of the reaction, precipitates were filtered and then the solvent was distilled off. The resultant residue was recrystallized from acetonitrile/diethyl ether to obtain 1.59 g (yield: 70%) of N-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate the physical properties of which are shown in Table 6.

Workup

  1. additionwas introduced at a rate of 50 ml/min. at -40° C. under vigorous stirring
  2. customAfter the completion of the reaction
  3. customprecipitates
  4. filtrationwere filtered
  5. distillationthe solvent was distilled off
  6. customThe resultant residue was recrystallized from acetonitrile/diethyl ether

Sources & evidence

ORD record
ord-b91908fd55ed454aaa45f42e0a2abe14
Source dataset
uspto-grants-1991_02
Patent number
US04996320

Reaction notes

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