Hydrochloric Acid → 9-[5-(4-Bromo-2-fluorophenoxy)-2-ethylphenyl]-3-oxaspiro[5.5]undecane-8,10-dione

HRID 537684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537684
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:21][CH3:22])=[C:6]([CH:8]2[C:18](=[O:19])[CH2:17][C:11]3([CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH2:10][C:9]2=[O:20])[CH:7]=1.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([F:31])[CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C1(C)C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O.CN(C)C=O.C(OCC)(=O)C>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:2]2[CH:3]=[CH:4][C:5]([CH2:21][CH3:22])=[C:6]([CH:8]3[C:18](=[O:19])[CH2:17][C:11]4([CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)[CH2:10][C:9]3=[O:20])[CH:7]=2)=[C:26]([F:31])[CH:25]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 27249814-Bromo-2-fluorophenolHCID 666799999-(5-Bromo-2-ethylphenyl)-3-oxaspiro[5.5]undecane-8,10-dione

Produkt 1

HCID 666792879-[5-(4-Bromo-2-fluorophenoxy)-2-ethylphenyl]-3-oxaspiro[5.5]undecane-8,10-dione

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2734996copper(II) trifluoromethanesulfonateKatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 9-(5-bromo-2-ethylphenyl)-3-oxaspiro[5.5]undecane-8,10-dione (360 mg, 0.99 mmol), 4-bromo-2-fluorophenol (227 mg, 1.19 mmol), cesium carbonate (645 mg, 1.98 mmol), copper(II) trifluoromethanesulfonate (18 mg, 0.05 mmol) and ethyl acetate (50 μl) in toluene (10 ml) is heated under reflux for 19 hours. The mixture is cooled to room temperature, N,N-dimethylformamide (2 ml) and 2M aqueous hydrochloric acid (10 ml) are added, and the mixture is stirred vigorously for 45 minutes. The mixture is extracted with ethyl acetate, and the organic extract is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by preparative reverse phase HPLC to give 9-[5-(4-bromo-2-fluorophenoxy)-2-ethylphenyl]-3-oxaspiro[5.5]undecane-8,10-dione.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 19 hours
  3. extractionThe mixture is extracted with ethyl acetate
  4. extractionthe organic extract
  5. dry with materialis dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure
  8. customThe residue is purified by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2d8ece02d33e4179abc47aa7d7d82784
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865623B2

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