Benzyl Alcohol → 4-(Benzyloxy)-2-bromonicotinonitrile

HRID 1020841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020841
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[N:19]=[CH:18][CH:17]=[C:16](Br)[C:13]=1[C:14]#[N:15]>CN(C=O)C>[CH2:3]([O:10][C:16]1[C:13]([C:14]#[N:15])=[C:12]([Br:11])[N:19]=[CH:18][CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 574595912,4-Dibromopyridine-3-carbonitrile

Produkt 1

HCID 230886954-(Benzyloxy)-2-bromonicotinonitrileAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of NaH (1.756 g, 45.818 mmol, mineral oil 60%) in DMF (200 ml) cooled at 0° C., was added benzyl alcohol (4.542 g, 42 mmol). The resulting mixture was stirred for 5 min. Then, intermediate compound D1 (10 g, 38.18 mmol) was added. The resulting reaction mixture was gradually warmed to r.t. and stirred for 1 h, then quenched with NH4Cl (aqueous sat. solution) and diluted with H2O. The resulting mixture was extracted with Et2O. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 1% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D2 (9.2 g, 83%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas gradually warmed to r.t.
  3. stirringstirred for 1 h
  4. customquenched with NH4Cl (aqueous sat. solution)
  5. additiondiluted with H2O
  6. extractionThe resulting mixture was extracted with Et2O
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 1% as eluent)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d9eb7bae8cb54383a70e854d6f9f5811
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716480B2

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