Sodium Carbonate → 2-(2,4-Dichlorophenyl)-6-chloro-3-nitropyridine

HRID 31846

Reaktionsgleichung

Reaktionsgleichung von HRID 31846
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 852392,6-Dichloro-3-nitropyridineHCID 2734659(2,4-Dichlorophenyl)boronic acid

Produkt 1

HCID 221429302-(2,4-Dichlorophenyl)-6-chloro-3-nitropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1 mmol 2,6-dichloro-3-nitropyridine, 1.05 mmol of 2,4-dichlorobenzeneboronic acid, and 3 mmol of Na2CO3, were dissolved in 1.5 ml THF and 0.5 ml water and purged with nitrogen. 0.05 mmol of [1,1′-Bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) was added to reaction and stirred at room temperature under nitrogen for fourteen hours. The reaction mixture was concentrated in vacuo and diluted with water and ethyl acetate. The solution was extracted three times with ethyl acetate, dried over sodium sulfate, and purified by column chromatography eluting with 10% ethylacetate 90% hexanes to obtain 2-(2,4-dichlorophenyl)-6-chloro-3-nitropyridine.

Aufarbeitung

  1. custom0.5 ml water and purged with nitrogen
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with water and ethyl acetate
  4. extractionThe solution was extracted three times with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. custompurified by column chromatography
  7. washeluting with 10% ethylacetate 90% hexanes

Quellen und Nachweise

ORD-Eintrag
ord-680c55eea424449eb93b061849d47654
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425557B2

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