Ethyl Acetate → 4-[4-(4-Bromo-2-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

HRID 512577

Reaktionsgleichung

Reaktionsgleichung von HRID 512577
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])=[C:4]([CH2:20][CH3:21])[CH:3]=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([F:30])[CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>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>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[O:11][C:10]([CH3:17])([CH3:18])[C:9]3=[O:19])=[C:4]([CH2:20][CH3:21])[CH:3]=2)=[C:25]([F:30])[CH:24]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27249814-Bromo-2-fluorophenolHCID 497653874-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

Produkt 1

HCID 497654624-[4-(4-Bromo-2-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2734996copper(II) trifluoromethanesulfonateKatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.42 g, 1.19 mmol), 4-bromo-2-fluorophenol (0.27 g, 1.43 mmol), cesium carbonate (0.78 g, 2.38 mmol), copper(II) trifluoromethanesulfonate (0.02 g, 0.06 mmol) and ethyl acetate (0.004 g, 0.06 mmol) in dry toluene (10 ml) are heated to reflux for 21 hours. The mixture is cooled to room temperature and N,N-dimethylformamide (2 ml) is added. The mixture is partitioned between 2M aqueous hydrochloric acid (10 ml) and ethyl acetate (3×10 ml). The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is purified by preparative reverse phase HPLC to give 4-[4-(4-bromo-2-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

Aufarbeitung

  1. temperatureare heated
  2. temperatureto reflux for 21 hours
  3. customThe mixture is partitioned between 2M aqueous hydrochloric acid (10 ml) and ethyl acetate (3×10 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customThe residue is purified by preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-aeed1d6718e2428195b1570d221349db
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102642B2

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