Water → 3-Chloro-6-(4-chlorophenyl)pyridazine

HRID 271703

Reaktionsgleichung

Reaktionsgleichung von HRID 271703
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](OB(O)O)=[CH:4][CH:3]=1.[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:12][C:13]1[N:14]=[N:15][C:16]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 17810664p-Chlorophenylboric acid

Produkt 1

HCID 122575023-Chloro-6-(4-chlorophenyl)pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Under an argon atmosphere a solution of 11.3 g (70.5 mmol) 4-chlorophenylboric acid in 50 mL 1,4-dioxane is added to a solution of 10.8 g (70.5 mmol) 3,6-dichloropyridazine, 10 mL (20 mmol) of a 2 M Na2CO3 solution and 600 mg (0.73 mmol) Pd(dppf)Cl2 in 150 mL 1,4-dioxane at 110° C. over 2 h. The reaction mixture is stirred for 1 h at 110° C. 100 mL water are added and the aqueous phase is extracted with 100 mL EtOAc. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Purification is carried out by column chromatography on silica gel (cyc/EtOAc 4:1).

Aufarbeitung

  1. extractionthe aqueous phase is extracted with 100 mL EtOAc
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-58f9c3b7b7de47869439a62f3987251e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452911B2

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