Water → Ethyl 5-chloro-2-methylnicotinate

HRID 660249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660249
Cl[C:2]1[N:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:14]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[Cl:13][C:10]1[CH:11]=[N:12][C:2]([CH3:14])=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 5200405Ethyl 2,5-dichloronicotinate

Produkt 1

HCID 53396281Ethyl 5-chloro-2-methylnicotinateAusbeute 37.958,301 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2,5-dichloronicotinate (step 1, 10 g, 0.045 mol), tetrakis(triphenylphoshine)palladium (5.2 g, 4.5 mmol), trimethylboroxine (5.65 g, 0.045 mmol) and potassium carbonate (18.66 g, 0.16 mmol) in 1,4-dioxane (contain 10% water, 100 ml) was refluxed for 7 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature and poured into water. The aqueous mixture was extracted with ethyl acetate. The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (50/1 to 20/1) to afford 3.41 g (38%) of the title compound:

Aufarbeitung

  1. temperaturewas refluxed for 7 h under nitrogen atmosphere
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (50/1 to 20/1)

Quellen und Nachweise

ORD-Eintrag
ord-e2306f648d474219bbc3751984273017
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084476B2

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