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2,5-Dibromopyridine → 5,5'-DIBROMO-2,2'-BIPYRIDINE

HRID 388185
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 388185
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=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.C1(C)C(C)=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)=[N:3][CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 693532,5-Dibromopyridine

Produkt 1

HCID 109031035,5'-DIBROMO-2,2'-BIPYRIDINEAusbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A reaction vessel was charged with 6.0 g of 2,5-dibromopyridine, 7.0 ml of bistributyltin, and 120 ml of xylene, followed by heating and stirring at 60° C. for 15 minutes. Further, 700 mg of tetrakis(triphenylphosphine)palladium was added thereto, followed by stirring at 120° C. for 8 hours. After cooling to room temperature, the insoluble materials were removed by filtration, and the filtrate was washed with 150 ml of an aqueous ethylenediamine tetraacetate solution. The organic layer was dehydrated with anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: cyclohexane/toluene) to obtain 1.7 g (yield 42%) of 5,5′-dibromo-[2,2′]bipyridine as a yellow powder.

Aufarbeitung

  1. temperatureby heating
  2. stirringby stirring at 120° C. for 8 hours
  3. temperatureAfter cooling to room temperature
  4. customthe insoluble materials were removed by filtration
  5. washthe filtrate was washed with 150 ml of an aqueous ethylenediamine tetraacetate solution
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a crude product
  8. customThe crude product was purified by column chromatography (carrier: silica gel, eluent: cyclohexane/toluene)

Quellen und Nachweise

ORD-Eintrag
ord-1ba185198f794398a9b7d1fc760388af
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08377573B2

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