Hydrochloric Acid → 2-(3,4-Dichlorophenoxy)-5-fluoro-benzoic acid

HRID 1839429

Reaktionsgleichung

Reaktionsgleichung von HRID 1839429
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[Cl:14].[F:16][C:17]1[CH:18]=[CH:19][C:20](I)=[C:21]([CH:25]=1)[C:22]([OH:24])=[O:23].Cl>C1(C)C=CC=CC=1.O.CCOC(C)=O.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[Cl:14])[O:15][C:20]1[CH:19]=[CH:18][C:17]([F:16])=[CH:25][C:21]=1[C:22]([OH:24])=[O:23]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 131585835-Fluoro-2-iodobenzoic acid2×

Produkt 1

HCID 220192772-(3,4-Dichlorophenoxy)-5-fluoro-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2734996copper(II) trifluoromethanesulfonateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under N2 in a round-bottomed flask fitted with a reflux condenser and magnetic stirrer were placed 6.37 g (19.55 mmol) of cesium carbonate and 3.2 g (19.55 mmol) of 3,4-dichlorophenol (both from Aldrich Chem. Co., Milwaukee, Wis.) in 60 mL of anhydrous toluene. After stirring the mixture for 5 min., 89 mg (0.24 mmol) of copper (II) trifluoromethansulfonate (copper triflate) and 0.26 g (9.78 mmol) of 5-fluoro-2-iodobenzoic acid (prepared according to the method in Collection of Czechoslovakian Chemical Communications, 1975, vol. 40, p728) were added and the mixture was heated to reflux overnight. Progress of the reaction was monitored using thin layer chromatography (tlc), eluting with CHCl3:CH3OH:AcOH (9:1:0.5). After allowing the reaction to cool to room temperature, the mixture was diluted with water and EtOAc; the aqueous layer was acidified with 6 N HCl and re-extracted with additional EtOAc. The organic layers were combined, washed with H2O and saturated NaCl and dried over MgSO4. Removal of the solvent in vacuo gave a dark brown colored oil, 2.6 g, as a mixture of title product and unreacted 5-fluoro-2-iodobenzoic acid.

Aufarbeitung

  1. customUnder N2 in a round-bottomed flask fitted with a reflux condenser and magnetic stirrer
  2. customaccording to the method in Collection of Czechoslovakian Chemical Communications, 1975, vol. 40, p728)
  3. additionwere added
  4. temperaturethe mixture was heated
  5. temperatureto reflux overnight
  6. washeluting with CHCl3:CH3OH:AcOH (9:1:0.5)
  7. customthe reaction
  8. extractionre-extracted with additional EtOAc
  9. washwashed with H2O and saturated NaCl
  10. dry with materialdried over MgSO4
  11. customRemoval of the solvent in vacuo
  12. customgave a dark brown colored oil, 2.6 g

Quellen und Nachweise

ORD-Eintrag
ord-d805be390d0b4af98bd5414a1e9eb7c2
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677378B2

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