Ethyl Acetate → (6-Bromo-3-methyl-benzofuran-2-yl)(2,4-dichloro-phenyl)methanone

HRID 29233

Reaktionsgleichung

Reaktionsgleichung von HRID 29233
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[C:4]([OH:11])[CH:3]=1.Cl[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])=[O:15].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]([CH3:9])=[C:13]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])=[O:15])[O:11][C:4]=2[CH:3]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 202502,2',4'-TrichloroacetophenoneHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Produkt 1

HCID 59788907(6-Bromo-3-methyl-benzofuran-2-yl)(2,4-dichloro-phenyl)methanoneAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 1-(4-Bromo-2-hydroxy-phenyl)-ethanone (2.81 g, 13.1 mmol, from step 1) and 2-chloro-1-(2,4-dichlorophenyl)ethanone (6.88 g, 30.8 mmol, 2.3 eq) in anhydrous N,N-dimethylformamide (50 mL) was added K2CO3 (7.42 g, 53.7 mmol, 4.0 eq). The dark brown reaction mixture was stirred at 90° C. for 38 h. The reaction was poured into ethyl acetate (100 mL) and water (100 mL) after cooled down to rt. Extracted with ethyl acetate (3×50 mL). The organic layer was dried (Na2SO4), filtered, and evaporated in vacuo. The crude product was washed by hexane (2×30 mL) followed by ethyl ether (2×30 mL) to provide 2.22 g (44%) of the desired compound as light yellow solid. 1H-NMR (CDCl3) δ 7.64 (d, J=1.9 Hz, 1H), 7.54 (d, J=8.7 Hz, 1H). 7.49 (d, J=1.9 Hz, 1H), 7.45-7.36 (m, 3H), 2.57 (s, 3H); MS LC-MS (MH+=385).

Aufarbeitung

  1. temperatureafter cooled down to rt
  2. extractionExtracted with ethyl acetate (3×50 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. washThe crude product was washed by hexane (2×30 mL)

Quellen und Nachweise

ORD-Eintrag
ord-f7c7f011aff84f57bf42d52d718405fa
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420066B2

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