Water → 6-(2,6-Difluorophenyl)-5-fluoropicolinic acid

HRID 1523509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523509
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([CH3:16])[N:10]=1.[O-:17][Mn](=O)(=O)=O.[K+].[OH2:23]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:10]=[C:11]([C:16]([OH:17])=[O:23])[CH:12]=[CH:13][C:14]=1[F:15]

Komponenten

4

Edukt 3

HCID 962WaterHCID 516875Potassium Permanganate2×HCID 592265082-(2,6-Difluorophenyl)-3-fluoro-6-methylpyridine

Produkt 1

HCID 592265526-(2,6-Difluorophenyl)-5-fluoropicolinic acidAusbeute 32 %

Versuchsvorschrift

To a solution of 2-(2,6-difluorophenyl)-3-fluoro-6-methylpyridine (1.0 equiv.) in water (0.05 M) was added KMnO4 (2.0 equiv.) and the reaction was heated to reflux overnight. Another 2.0 equiv. of KMnO4 were added and stirred at reflux for another 8 hours. The solution was cooled to room temperature, filtered through Celite and washed with water. The filtrate was acidified with 6N HCl to pH=3, the white precipitate was filtered. The filtrate was further acidified to pH=1 and filtered again. The filtrate was extracted with ethyl acetate until no more product in the aqueous layer. The organic phase was washed with brine and dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in ethyl acetate, washed with 1N NaOH, the aqueous layer was acidified to pH=1 and the white crystals were filtered. The combined products yielded 6-(2,6-difluorophenyl)-5-fluoropicolinic acid in 32% yield as a white solid. LC/MS=254.0 (M+H), Rt=0.71 min.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. temperatureat reflux for another 8 hours
  4. filtrationfiltered through Celite
  5. washwashed with water
  6. filtrationthe white precipitate was filtered
  7. filtrationfiltered again
  8. extractionThe filtrate was extracted with ethyl acetate until no more product in the aqueous layer
  9. washThe organic phase was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. dissolutionThe residue was dissolved in ethyl acetate
  14. washwashed with 1N NaOH
  15. filtrationthe white crystals were filtered

Quellen und Nachweise

ORD-Eintrag
ord-b04785caf1c14afb9722255a6e9f16ff
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079889B2

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