2,3-Difluorophenol → 2-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-ethanone

HRID 14457

Reaktionsgleichung

Reaktionsgleichung von HRID 14457
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](Cl)=[O:14])=[CH:8][CH:7]=1.[F:16][C:17]1[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=1[OH:24]>ClCCCl.O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([C:19]2[CH:20]=[CH:21][C:22]([F:23])=[C:17]([F:16])[C:18]=2[OH:24])=[O:14])=[CH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 808792,3-DifluorophenolHCID 906924-Chlorophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 686985132-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of aluminium chloride (7.66 g, 57.4 mmol, 1.5 eq.) and (4-chlorophenyl)acetyl chloride (8.7 g, 46 mmol, 1.2 eq.) in 1,2-dichloroethane (75 ml) is stirred at 0° C. for 30 min. A solution of 2,3-difluorophenol (5 g, 38.4 mmol) in 1,2-dichloroethane (25 ml) is added to the reaction mixture, which is heated in an oil bath at 90° C. overnight. The reaction mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic phase is dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford a brown solid. This is triturated with hexane/ethyl acetate (9:1), filtered and dried to afford the title compound as a pale brown fine solid which is 87% pure by HPLC analysis.

Aufarbeitung

  1. temperatureis heated in an oil bath at 90° C. overnight
  2. temperatureThe reaction mixture is cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customto afford a brown solid
  8. customThis is triturated with hexane/ethyl acetate (9:1)
  9. filtrationfiltered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9bbf5b40766140ed82fefb6b7021adb9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732435B2

Verknüpfte Notizen

Wird geladen…