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

HRID 1873394

Reaktionsgleichung

Reaktionsgleichung von HRID 1873394
Br[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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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 1370132-BromoselenopheneHCID 15135235B-(4-Ethoxy-2,3-difluorophenyl)boronic acid

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of 45.0 g (0.21 mol) of 2-bromoselenophene, 52.0 g (0.26 mol) of 4-ethoxy-2,3-difluorophenylboronic acid, 20.0 g (17.3 mmol) of tetrakis(triphenylphosphine)palladium(0) and 600 ml of 2 N sodium carbonate soln. in 1100 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with sat. sodium hydrogencarbonate soln., 1 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:toluene=3:2). Further purification is carried out by recrystallisation from ethanol; 2-(4-ethoxy-2,3-difluorophenyl)selenophene is obtained as a beige solid.

Aufarbeitung

  1. temperatureunder reflux for 20 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted with toluene
  5. washThe combined organic phases are washed with sat. sodium hydrogencarbonate soln
  6. customThe solution is dried
  7. concentrationconcentrated to dryness
  8. customThe residue is purified by column chromatography (SiO2, n-heptane:toluene=3:2)
  9. customFurther purification
  10. customis carried out by recrystallisation from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b0d75b2282834822b4ffc49a3ff86c7a
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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