Ethyl difluoroacetate → HCID 86638499, Verbindung

HRID 216344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216344
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Li]CCCC.[F:14][CH:15]([F:21])[C:16](OCC)=[O:17]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:16](=[O:17])[CH:15]([F:21])[F:14])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 9961Ethyl difluoroacetateHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Produkt 1

HCID 86638499HCID 86638499, VerbindungAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2,5-dibromopyridine (15.21 g, 64 mmol) in anhydrous toluene (150 mL) at −78° C. under nitrogen was added dropwise with n-BuLi (2.5 M in hexane, 25 mL, 62 mmol). Stirring was continued at −78° C. for 2 h, then ethyl difluoroacetate (11 g, 80 mmol) was added dropwise at −78° C. The mixture was stirred overnight while the temperature rose to room temperature. The mixture was partitioned between EtOAc and brine, the water layer was extracted with EtOAc, the combined organic extracts were dried and concentrated, flash chromatography on silica gel afforded 8.53 g of 1-(5-bromopyridin-2-yl)-2,2-difluoroethanone as white solid.

Aufarbeitung

  1. stirringThe mixture was stirred overnight while the temperature
  2. customrose to room temperature
  3. customThe mixture was partitioned between EtOAc and brine
  4. extractionthe water layer was extracted with EtOAc
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb5e77370f144043b51db303a0569305
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193228B2

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