Potassium Fluoride → 2-Cyano-5-fluoropyridine

HRID 887641Notes

Reaction equation

HRID 887641 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[F-:10].[K+]>CN1CCCC1=O.O>[F:10][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 8171545-Bromopyridine-2-carbonitrile

Product 1

HCID 113324532-Cyano-5-fluoropyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
175 °C

Procedure

The mixture of 5-bromo-pyridine-2-carbonitrile (0.50 g, 2.73 mmol), and KF (0.48 g, 8.20 mmol) in 10 ml of 1-methyl-2-pyrrolidinone was stirred at 175° C. for 18 h, cooled to RT, diluted with H2O, extracted with EtOAc, the combined organic portions were washed with H2O, brine, dried with Na2SO4, filtered, condensed, the crude compound was purified by flash column chromatography (5 to 20% of EtOAc in hexanes). The titled compound was obtained as an off-white solid.

Workup

  1. temperaturecooled to RT
  2. extractionextracted with EtOAc
  3. washthe combined organic portions were washed with H2O, brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customcondensed
  7. customthe crude compound was purified by flash column chromatography (5 to 20% of EtOAc in hexanes)

Sources & evidence

ORD record
ord-272194c878f9426babb03d19241fa87e
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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