Sodium hydride → 4-(5-Fluoro-pyridin-2-yloxymethyl)-benzonitrile

HRID 77934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77934
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[OH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.[H-].[Na+]>CN(C)C=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([O:9][CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 160549p-Cyanobenzyl alcoholHCID 27831712-Bromo-5-fluoropyridine

Produkt 1

HCID 592554234-(5-Fluoro-pyridin-2-yloxymethyl)-benzonitrileAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To an N,N-dimethylformamide (50 mL) solution of 2-bromo-5-fluoropyridine (5 g, 28.4 mmol) and 4-(hydroxymethyl)-benzonitrile (5.67 g, 42.4 mmol) was added sodium hydride (1.7 g, 42.4 mmol, 60% in oil) at room temperature. The mixture was stirred for 3 hours at 70° C. The mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=4:1-2:1-1:1-ethyl acetate) to obtain the title compound (5.5 g, 85%).

Aufarbeitung

  1. customThe mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=4:1-2:1-1:1-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a260c6188b424fffbb655065652eba38
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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