Ethanol → 2,3,4,6-Tetrafluorobenzoic acid ethyl ester

HRID 10269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 10269
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[C:7]([F:13])[C:3]=1[C:4]([OH:6])=[O:5].[C:14](Cl)(=O)[C:15](Cl)=O.C(O)C.C([O-])(O)=O.[Na+]>ClCCl.CN(C)C=O.C1C=CC=CC=1>[CH2:14]([O:5][C:4](=[O:6])[C:3]1[C:7]([F:13])=[CH:8][C:9]([F:12])=[C:10]([F:11])[C:2]=1[F:1])[CH3:15]

Komponenten

8

Edukt 4

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 27765912,3,4,6-tetrafluorobenzoic Acid

Produkt 1

HCID 210411752,3,4,6-Tetrafluorobenzoic acid ethyl esterAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 241BenzeneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2,3,4,6-Tetrafluorobenzoic acid (4.8 g, 24.7 mmol) in dichloromethane (80 mL) is cooled to 0° C. under a nitrogen atmosphere and treated with oxalyl chloride (11.2 mL, 128 mmol) followed by anhydrous N,N-dimethylformamide (2 drops). The mixture is warmed to room temperature and stirred for 2 hours. The solution is co-evaporated with benzene to yield an oil that is taken up in dichloromethane (80 mL), cooled to 0° C. under an inert atmosphere, and treated with anhydrous ethanol (15 mL, 258 mmol). After 5 hours at room temperature, the solution is poured into saturated NaHCO3 and extracted with chloroform. The organic phase is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to provide the title compound (3.3 g). This material is used without further purification. 1H NMR (CDCl3): δ 6.93–6.75 (m, 1H), 4.42 (q, 2H), 1.39 (t, 3H).

Aufarbeitung

  1. customto yield an oil that
  2. temperaturecooled to 0° C. under an inert atmosphere
  3. waitAfter 5 hours at room temperature
  4. extractionextracted with chloroform
  5. washThe organic phase is washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-58a59fa4c9c44e9090ed4436fa020b49
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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