Ethoxalyl chloride → Ethyl 3,5-dibromo-alpha-oxo-2-thiopheneacetate

HRID 590984

Reaktionsgleichung

Reaktionsgleichung von HRID 590984
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[S:7][CH:8]=[C:9]([Br:11])[CH:10]=1.Cl[C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>ClCCl>[Br:11][C:9]1[CH:10]=[C:6]([Br:5])[S:7][C:8]=1[C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Komponenten

5

Edukt 3

HCID 20884Ethoxalyl chlorideHCID 2724560Thiophene, 2,4-dibromo-HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 14113379Ethyl 3,5-dibromo-alpha-oxo-2-thiopheneacetateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Aluminium chloride (0.26 g, 1.98 mmol) was added to a solution of 2,4-dibromothiophene (0.30 g, 1.24 mmol) and ethyl chlorooxoacetate (0.19 g, 1.36 mmol) in dichloromethane (10 mL) previously cooled with an ice bath. The reaction mixture was stirred at room temperature 45 minutes, poured into ice water and extracted with dichloromethane (2×20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to provide the desired keto-ester (10a) (0.42 g, 1.24 mmol, 100%) as a yellow oil.

Aufarbeitung

  1. temperaturepreviously cooled with an ice bath
  2. extractionextracted with dichloromethane (2×20 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d74ffaa69872415e9aebab0a935931fd
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

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