2,4-Dichloro-1-(2,2-dibromovinyl)benzene → 2,4-Dichloro-1-ethynylbenzene

HRID 275689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275689
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11].C([Li])CCC>C1COCC1>[Cl:11][C:5]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[C:3]#[CH:2]

Komponenten

4

Edukt 2

HCID 120184412,4-Dichloro-1-(2,2-dibromovinyl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 126397532,4-Dichloro-1-ethynylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 1,1-dibromo-2-(2,4-dichlorophenyl)ethene (14 g, 42.4 mmol) in THF (100 ml) at −78° C. under nitrogen was treated with butyllithium (1.6 M solution in hexane, 28 ml, 44.8 mmol). after being stirred for 1 hour at −78° C, the reaction mixture was warmed to room temperature and stirred for another hour. The reaction was quenched with water and the product was extracted with hexanes. The extract was dried over MgSO4, filtrated and concentrated in vacuo to give the product. (Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769)

Aufarbeitung

  1. temperaturethe reaction mixture was warmed to room temperature
  2. stirringstirred for another hour
  3. customThe reaction was quenched with water
  4. extractionthe product was extracted with hexanes
  5. dry with materialThe extract was dried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo
  8. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-f96ddd35dd0c48529e1aea558c55913b
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352990B1

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