Methyl 4-(chlorocarbonyl)benzoate → HCID 46193254, Verbindung

HRID 555649

Reaktionsgleichung

Reaktionsgleichung von HRID 555649
[Se:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH3:6][O:7][C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)=[O:9].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Se:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:14]([C:13]1[CH:12]=[CH:11][C:10]([C:8]([O:7][CH3:6])=[O:9])=[CH:18][CH:17]=1)=[O:15]

Komponenten

5

Edukt 3

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 136130SelenopheneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 46193254HCID 46193254, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Selenophene (61) (5.0 g, 0.038 mole) and 4-methoxycarbonyl benzoyl chloride (62) (8.34 g, 0.042 mole) were dissolved in 50 ml of 1, 2-dichloroethane, and then anhydrous aluminum chloride (AlCl3) (10.19 g, 0.076 mole) was added. The mixture was heated under refluxing for 30 min, cooled, and quenched with 250 ml of icewater to stop the reaction. The organic layer was sequentially washed with water, 5% sodium carbonate solution, and water till neutral, then dried over MgSO4 and filtered. The solvent of the filtrate was evaporated under a reduced pressure, and the residue was subjected to a column chromatography (silica gel, chloroform), and then recrystallized from n-hexane to afford compound 63 in yellow crystals (4.78 g).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for 30 min
  3. temperaturecooled
  4. customquenched with 250 ml of icewater
  5. customthe reaction
  6. washThe organic layer was sequentially washed with water, 5% sodium carbonate solution, and water till neutral,
  7. dry with materialthen dried over MgSO4
  8. filtrationfiltered
  9. customThe solvent of the filtrate was evaporated under a reduced pressure
  10. customrecrystallized from n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1f68cc05017a43f6a9a3bbe22ebe697c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053459B1

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