Sodium Carbonate → 2-(4-Ethoxy-2,3-difluorophenyl)selenophene

HRID 1873393

Reaktionsgleichung

Reaktionsgleichung von HRID 1873393
I[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[C:12]([F:19])[C:11]=1[F:20])[CH3:8].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CC(OC)(C)C>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[Se:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([F:19])[C:11]=1[F:20])[CH3:8]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 1421832-IodoselenopheneHCID 15135235B-(4-Ethoxy-2,3-difluorophenyl)boronic acid

Produkt 1

HCID 594563012-(4-Ethoxy-2,3-difluorophenyl)selenophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15413tert-Butyl methyl etherLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of 34.8 g (0.14 mol) of 2-iodoselenophene, 32.8 g (0.16 mol) of 4-ethoxy-2,3-difluorophenylboronic acid, 8.10 g (77.01 mmol) of tetrakis -(triphenylphosphine)palladium(0) and 300 ml of 2 N sodium carbonate soln. in 800 ml of toluene/ethanol (1:1) is heated under reflux for 23 h. The mixture is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with 2 N hydrochloric acid and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:EtOAc=15:1-10:1→5:1). Further purification is carried out by recrystallisation from n-heptane; 2-(4-ethoxy-2,3-difluorophenyl)selenophene is obtained as a beige solid.

Aufarbeitung

  1. temperatureunder reflux for 23 h
  2. washwashed with water
  3. extractionThe aqueous phase is extracted with MTBE
  4. washthe combined organic phases are washed with 2 N hydrochloric acid and sat. sodium chloride soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by column chromatography (SiO2, n-heptane:EtOAc=15:1-10:1→5:1)
  8. customFurther purification
  9. customis carried out by recrystallisation from n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-0762230a08e74588a5910f25485ffb77
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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