3,4-Dichlorophenol → 2-[5-(3,4-Dichlorophenoxy)-2-ethylphenyl]cyclopentane-1,3-dione

HRID 339469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339469
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH3:16])=[C:6]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:7]=1.[Cl:17][C:18]1[CH:19]=[C:20]([OH:25])[CH:21]=[CH:22][C:23]=1[Cl:24].C(=O)([O-])[O-].[Cs+].[Cs+]>[O-]S(C(F)(F)F)(=O)=O.[Cu+2].[O-]S(C(F)(F)F)(=O)=O.C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:23]=1[Cl:24])[O:25][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH3:16])=[C:6]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:7]=1

Komponenten

6

Edukt 3

HCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 666773502-(5-Bromo-2-ethylphenyl)cyclopentane-1,3-dione

Produkt 1

HCID 666767552-[5-(3,4-Dichlorophenoxy)-2-ethylphenyl]cyclopentane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734996copper(II) trifluoromethanesulfonateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a mixture of 2-(5-bromo-2-ethylphenyl)cyclopentane-1,3-dione (0.200 g, 0.71 mmol), 3,4-dichlorophenol (0.577 g, 3.56 mmol), cesium carbonate (0.502 g, 1.42 mmol), copper triflate (13 mg, 0.04 mmol) and activated (powdered) 5 Å molecular sieves (0.400 g) is added anhydrous toluene (2.5 ml). The reaction mixture is purged with nitrogen then heated at 160° C. for 1 hour under microwave irradiation. After cooling to room temperature dichloromethane is added and mixture is quenched with 2M aqueous hydrochloric acid then filtered. The organic phase is concentrated under reduced pressure to give a crude oil which is purified by preparative reverse-phase HPLC to afford 2-[5-(3,4-dichlorophenoxy)-2-ethylphenyl]cyclopentane-1,3-dione.

Aufarbeitung

  1. customThe reaction mixture is purged with nitrogen
  2. temperatureAfter cooling to room temperature dichloromethane
  3. additionis added
  4. custommixture is quenched with 2M aqueous hydrochloric acid
  5. filtrationthen filtered
  6. concentrationThe organic phase is concentrated under reduced pressure
  7. customto give a crude oil which
  8. customis purified by preparative reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f360613ab512475eb52e2deac87ff588
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895474B2

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