Sodium Carbonate → HCID 59456297, Verbindung

HRID 1873411

Reaktionsgleichung

Reaktionsgleichung von HRID 1873411
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[C:13]([F:14])=[C:12]([O:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.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>[F:7][C:8]1[C:13]([F:14])=[C:12]([O:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:9]=1[C:19]1[CH:20]=[CH:21][C:22]([C:2]2[Se:3][CH:4]=[CH:5][CH:6]=2)=[CH:23][CH:24]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 1370132-BromoselenopheneHCID 684879992',3'-Difluoro-4'-propoxybiphenyl-4-ylboronic acid

Produkt 1

HCID 59456297HCID 59456297, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A mixture of 12.7 g (60.6 mmol) of 2-bromoselenophene, 17.7 g (60.6 mmol) of 2′,3′-difluoro-4′-propoxybiphenyl-4-ylboronic acid, 5.55 g (4.80 mmol) of tetrakis(triphenylphosphine)palladium(0) and 180 ml of 2 N sodium carbonate soln. in 600 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 chloride soln., and the solution is dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). Further purification is carried out by recrystallisation from n-heptane:EtOH=3:1. 2-(2′,3′-Difluoro-4′-propoxybiphenyl-4-yl)selenophene is obtained as a yellow 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 chloride soln
  6. custom, and the solution is dried
  7. concentrationThe solution is concentrated to dryness
  8. customthe residue is purified by column chromatography (SiO2, toluene)
  9. customFurther purification
  10. customis carried out by recrystallisation from n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-6cde7b42f3c24904b3a5fe38330bf45c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304036B2

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