Imidazole → Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-

HRID 379037

Reaktionsgleichung

Reaktionsgleichung von HRID 379037
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1>CN(C=O)C>[F:11][C:5]1[CH:4]=[C:3]([CH2:2][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Komponenten

4

Edukt 2

HCID 795ImidazoleHCID 27784664-Cyano-3-fluorobenzyl bromide

Produkt 1

HCID 21697068Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Bromomethyl-2-fluoro-benzonitrile (3.44 g, 16.0 mmol) and imidazole (5.47 g, 80.3 mmol) were dissolved in DMF (40 mL) and stirred at ambient temperature for 2 h. The DMF was removed in vacuo and the residue was partitioned between EtOAc (300 mL) and aqueous saturated NaHCO3 solution. The organic layer was separated, washed with NaHCO3 solution, H2O, brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound after chromatography (silica gel, 1-2% CH3OH/CH2Cl2).

Aufarbeitung

  1. customThe DMF was removed in vacuo
  2. customthe residue was partitioned between EtOAc (300 mL) and aqueous saturated NaHCO3 solution
  3. customThe organic layer was separated
  4. washwashed with NaHCO3 solution, H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6172a76ce1384a90bbceeb45ea67674d
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297239B1

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