Potassium Fluoride → 4-Cyano-2-fluoropyridine

HRID 736992Notes

Reaction equation

HRID 736992 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[F-:10].[K+]>CN1CCCC1=O.[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.O>[F:10][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]#[N:9]

Participants

6

Reactant 2

HCID 522689Potassium FluorideHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 120025874-Cyano-2-fluoropyridineYield 43.3%

Reagents, catalysts & solvents 3

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

Treat a solution of 2-chloro-4-cyanopyridine (6.0 g, 43.5 mmol) and potassium fluoride (7.56 g, 130.3 mmol) in 1-methyl-2-pyrrolidinone (20 mL) with tetrabutylphosphonium bromide (14.8 g, 43.7 mmol) and heat to 100° C. for 18 hours. Dilute with water and extract with EtOAc. Wash EtOAc with water, brine, dry with Na2SO4, and concentrate to give the title compound (2.3 g, 43%). MS (ES) 123.1 (M+1)+. 1H NMR (400 MHz, CHCl3) δ 8.43 (d, 1H, J=5.2 Hz), 7.45 (m, 1H), 7.22 (m, 1H).

Workup

  1. extractionextract with EtOAc
  2. dry with materialWash EtOAc with water, brine, dry with Na2SO4
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-60458a972c0245d5bccfb757d0389d49
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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