1,2-Dibromoethane → HCID 67997471, Verbindung

HRID 1528601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528601
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=1)[CH3:4].Br[CH2:17][CH2:18]Br>CN(C)C=O>[CH2:3]([O:5][C:6]([C:7]1([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=2)[CH2:18][CH2:17]1)=[O:15])[CH3:4]

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 53419398Ethyl 2-(4-broMopyridin-2-yl)acetate

Produkt 1

HCID 67997471HCID 67997471, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (55% in mineral oil, 0.72 g) was added to a solution of (4-bromo-pyridin-2-yl)-acetic acid ethyl ester (1.80 g) in N,N-dimethylformamide (20 mL) chilled in an ice bath. The resulting mixture was stirred for 10 min at room temperature and then cooled again in an ice bath. 1,2-Dibromoethane (0.70 mL) was added dropwise and the cooling bath was removed. The mixture was stirred at room temperature overnight. Brine was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→1:1) to give the title compound as an oil. Yield: 1.28 g (64% of theory); Mass spectrum (ESI+): m/z=270/272 (Br) [M+H]+.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. temperaturecooled again in an ice bath
  3. customthe cooling bath was removed
  4. stirringThe mixture was stirred at room temperature overnight
  5. additionBrine was added
  6. extractionthe resulting mixture was extracted with ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated
  10. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-907aa1701e444803b47522d7169a4d53
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090605B2

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