4-Bromophenacyl bromide → Ethyl 2-acetyl-4-(4-bromophenyl)-4-oxobutanoate

HRID 18639

Reaktionsgleichung

Reaktionsgleichung von HRID 18639
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:14]([CH:13]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4])[C:12]([O:18][CH2:19][CH3:20])=[O:17])(=[O:15])[CH3:16]

Komponenten

5

Edukt 3

HCID 74544-Bromophenacyl bromideHCID 8868Ethyl AcetoacetateHCID 11430Potassium Carbonate

Produkt 1

HCID 14173974Ethyl 2-acetyl-4-(4-bromophenyl)-4-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 2,4′-dibromoacetophenone (3.0 g, 10.8 mmol), ethyl acetoacetate (1.48 mL, 10.8 mmol) and potassium carbonate (4.5 g, 32.4 mmol) were heated in 2-butanone (50 mL) at reflux for 24 hours. Upon cooling, the mixture was filtered over diatomaceous earth and concentrated. The residue was purified by chromatography with DCM to provide the title compound as an oil. 1H NMR (CDCl3) δ ppm 1.30 (3H), 2.10 (3H), 3.19 (2H), 3.75 (1H), 4.15 (2H), 7.50 (2H), 7.81 (2H); MS (ESI) m/z 326/328.

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. temperatureUpon cooling
  3. filtrationthe mixture was filtered over diatomaceous earth
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography with DCM

Quellen und Nachweise

ORD-Eintrag
ord-bfcda754581f492fbdf500441de8d793
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741364B2

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