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

HRID 587623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587623
[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 compound D1 (10 g, 38.18 mmol) was quickly added. The resulting reaction mixture was gradually warmed to r.t. and stirred for 1 h. The reaction mixture was quenched with NH4Cl (aqueous sat. solution), diluted with H2O and 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. customThe reaction mixture was quenched 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-c162d6edbb1b4c80a4a0cb9547a0fcf0
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226930B2

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