Toluene → O-Terphenyl

HRID 1253379

Reaktionsgleichung

Reaktionsgleichung von HRID 1253379
C([O-])([O-])=O.[Na+].[Na+].[C:7]1([CH3:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>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>[C:7]1([C:13]2[C:13]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:12][CH:7]=[CH:8][CH:9]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 1140TolueneHCID 10340Sodium Carbonate

Produkt 1

HCID 6766O-TerphenylAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

6.4 mmol of the dibromide (VI) and 6.4 mmol of the arylboronic acid derivative (V) (2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)pyridine) are dissolved in 25 ml of toluene. 0.4 mmol of Pd(PPh3)4 and 10 ml of a 4N solution of Na2CO3 are added, and the mixture is heated up to reflux under nitrogen. The reaction mixture is heated under reflux for 6 hours and cooled, the phases formed are separated, and the water phase is extracted with dichloromethane and dried. The solvent is removed under reduced pressure and the crude product is purified by means of a short silica gel column. After purification by column chromatography (dichloromethane/hexane, 2:1), the desired o-terphenyl derivative is obtained in from 40 to 50% yield.

Aufarbeitung

  1. temperaturethe mixture is heated up
  2. temperatureto reflux under nitrogen
  3. temperatureThe reaction mixture is heated
  4. temperatureunder reflux for 6 hours
  5. temperaturecooled
  6. customthe phases formed
  7. customare separated
  8. extractionthe water phase is extracted with dichloromethane
  9. customdried
  10. customThe solvent is removed under reduced pressure
  11. customthe crude product is purified by means of a short silica gel column
  12. customAfter purification by column chromatography (dichloromethane/hexane, 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-01f1ee677a1542aa90333940b0032771
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455112B2

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