1-Bromo-2-Chloroethane → 1-(2-Furyl)cyclopropanecarbonitrile

HRID 2393119

Reaktionsgleichung

Reaktionsgleichung von HRID 2393119
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]#[N:8].Br[CH2:10][CH2:11]Cl.[H-].[Na+]>CS(C)=O.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([C:7]#[N:8])[CH2:11][CH2:10]1

Komponenten

6

Edukt 3

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 109095152-Furanacetonitrile

Produkt 1

HCID 189756811-(2-Furyl)cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of furan-2-acetonitrile (28.4 g) and 1-bromo-2-chloroethane (33.1 ml) in dimethyl sulphoxide (50 ml) was added slowly to a stirred suspenson of sodium hydride (60% dispersion in mineral oil ; 31.85 g) in dry dimethyl sulphoxide (300 ml) keeping the internal temperature just below 35° C. by occasional cooling. After stirring for 18 hours at ambient temperature the mixture was diluted with water (500 ml) and extracted with ether (1×200 then 2×100 ml). The combined extracts were dried over potassium carbonate and evaporated to an oil which was distilled at reduced pressure to give 1-(2-furyl)cyclopropanecarbonitrile (28.0 g) as a colourless oil, bp 54° C./0.55 mbar.

Aufarbeitung

  1. customthe internal temperature just below 35° C.
  2. extractionextracted with ether (1×200
  3. dry with materialThe combined extracts were dried over potassium carbonate
  4. customevaporated to an oil which
  5. distillationwas distilled at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f58047de4e2f4ad2b5120e238022491b
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05804586

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