3,6-Dichloropyridazine → 3-Chloro-6-(2,6-difluorobenzyl)pyridazine

HRID 1454962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454962
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[Br-].[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=1[CH2:13][Zn+]>C1COCC1.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>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:13][C:12]2[C:11]([F:10])=[CH:18][CH:17]=[CH:16][C:15]=2[F:19])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 673313,6-DichloropyridazineHCID 178505728HCID 178505728, Verbindung

Produkt 1

HCID 575312393-Chloro-6-(2,6-difluorobenzyl)pyridazineAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3,6-dichloro pyridazine (7.39 g, 50 mmol) and tetrakis(triphenylphosphine)palladium (2.89 g, 2.5 mmol) in THF (500 mL) was added 2,6 difluoro benzyl zinc bromide (120 mL, 60 mmol). The reaction mixture was heated to 80° C. for 1.5 hours until the reaction was complete by TLC. The reaction was cooled to room temperature, filtered through celite, and concentrated in vacuo. The crude residue was recrystalized from ether to yield 5.7 g of the title compound.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was recrystalized from ether

Quellen und Nachweise

ORD-Eintrag
ord-e439f29fbc714d119ad8d5fca1ddaff8
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482345B2

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