Ammonium Chloride → 1-(5-Bromopyridin-2-yl)cyclopropane-1-carbonitrile

HRID 1425953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425953
C[Si](C)(C)[N-][Si](C)(C)C.[K+].[Br:11][C:12]1[CH:13]=[CH:14][C:15](F)=[N:16][CH:17]=1.[CH:19]1([C:22]#[N:23])[CH2:21][CH2:20]1.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[N:16][CH:17]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 79637CyclopropanecarbonitrileHCID 27831685-Bromo-2-fluoropyridineHCID 3251421Potassium bis(trimethylsilyl)amide

Produkt 1

HCID 534029901-(5-Bromopyridin-2-yl)cyclopropane-1-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Potassium hexamethyldisilazide (0.5 mol/L in toluene, 34 mL) was added over a period of 5 min to a solution of 5-bromo-2-fluoro-pyridine (1.50 g) and cyclopropanecarbonitrile (0.63 mL) in toluene (2 mL) chilled in an ice bath. Aqueous NH4Cl solution was then added and the resulting mixture was extracted with ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent was evaporated. The residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:0→8:2) to give the title compound as a colorless solid. Yield: 0.19 g (10% of theory); LC (method 2): tR=3.34 min; Mass spectrum (ESI+): m/z=223/225 (Br) [M+H]+.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 1:0→8:2)

Quellen und Nachweise

ORD-Eintrag
ord-8d043d621b944cd89e97c7878bd63368
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933072B2

Notizen zur Reaktion

Wird geladen…