Dimethylformamide → Tert-butyl 3-chloro-2,4-difluorobenzoate

HRID 240585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240585
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[Cl:15][C:16]1[C:17]([F:26])=[C:18]([CH:22]=[CH:23][C:24]=1[F:25])C(O)=O.CN(C=O)C>C([O-])(O)=O.[Na+].CCOC(C)=O>[Cl:15][C:16]1[C:24]([F:25])=[C:23]([CH:22]=[CH:18][C:17]=1[F:26])[C:6]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:5]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 27735323-Chloro-2,4-difluorobenzoic acid

Produkt 1

HCID 58046346Tert-butyl 3-chloro-2,4-difluorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 125 mL, single-neck, round-bottomed flask was charged with di-tert-butoxy-N,N-dimethylmethanamine (48.2 ml, 201 mmol), 3-chloro-2,4-difluorobenzoic acid (9.67 g, 50.2 mmol), and DMF (50 ml). The reaction was heated to 80° C. for 48 hours. After cooling to ambient temperature, the reaction was diluted with saturated NaHCO3 and EtOAc. The aqueous phase was extracted with EtOAc, and the combined organic phases were washed with saturated NaHCO3 and brine, dried, filtered and concentrated to provide the desired product as a gold oil.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organic phases were washed with saturated NaHCO3 and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fa4412622b96455780588c4a1f85a6ca
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648087B2

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