Ammonium Chloride → 3-Chloro-2-methoxy-4,6-dimethylpyridine

HRID 1043894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043894
Br[C:2]1[C:3]([CH3:12])=[N:4][C:5]([O:10][CH3:11])=[C:6]([Cl:9])[C:7]=1[CH3:8].C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[Cl:9][C:6]1[C:5]([O:10][CH3:11])=[N:4][C:3]([CH3:12])=[CH:2][C:7]=1[CH3:8]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 866863283-Bromo-5-chloro-6-methoxy-2,4-dimethylpyridineHCID 178418339Butyllithium

Produkt 1

HCID 866863293-Chloro-2-methoxy-4,6-dimethylpyridineAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

3-bromo-5-chloro-6-methoxy-2,4-dimethylpyridine (930 mg) was added to THF (10 mL). The solution was cooled to −78° C., and n-butyllithium (2.6 M solution in n-hexane, 1.428 mL) was added, followed by stirring at the same temperature for one hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with DCM. The organic layer was washed with brine and dried over sodium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (300 mg).

Aufarbeitung

  1. extractionfollowed by extraction with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%)

Quellen und Nachweise

ORD-Eintrag
ord-6c64f2a183194f179e74453f3fed0a5a
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563565B2

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