Hydrochloric Acid → Ethyl 4-chloro-3,5-difluoropicolinate

HRID 1522564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522564
[F:1][C:2]1C(C#N)=[N:4][CH:5]=[C:6]([F:9])[C:7]=1I.[ClH:12].[O:13]1CCO[CH2:15][CH2:14]1.[CH3:19][CH2:20][OH:21]>>[Cl:12][C:7]1[C:6]([F:9])=[CH:5][N:4]=[C:19]([C:20]([O:13][CH2:14][CH3:15])=[O:21])[C:2]=1[F:1]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 312751,4-DioxaneHCID 674695943,5-Difluoro-4-iodopicolinonitrile

Produkt 1

HCID 67469638Ethyl 4-chloro-3,5-difluoropicolinate

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3,5-difluoro-4-iodopicolinonitrile (8.0 g, 30.1 mmol) in EtOH (50 mL) was added 4N HCl in 1,4-dioxane (50 mL, 30.1 mmol) and the mixture was heated at 60° C. for 15 hours. The reaction was cooled to room temperature and evaporated under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with saturated NaHCO3 solution (100 mL) and brine. The organics were combined and dried over Na2SO4 and evaporated. This material was purified on silica gel chromatography eluted with hexane/EtOAc (0-100%) to give ethyl 4-chloro-3,5-difluoropicolinate. MS [M+H] found 222.1.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed with saturated NaHCO3 solution (100 mL) and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThis material was purified on silica gel chromatography
  8. washeluted with hexane/EtOAc (0-100%)

Quellen und Nachweise

ORD-Eintrag
ord-24499dc872f742ab966887d77b55f0eb
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073918B2

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