Reaktion #1712975

Reaktionsgleichung

ammonium chloride

n-butyl lithium

thieno[3,2-b]thiophene

hexachloroethane

→

2-Chlorothieno[3,2-b]thiophene

Ausbeute 75.4%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled again to −78° C
2. 2
   workup.ADDITIONAdded
3. 3
   workup.STIRRINGThe mixture was stirred at the same temperature for one hour
4. 4
   Temperaturwarmed to 0° C
5. 5
   workup.ADDITIONAdded
6. 6
   Extraktionthe mixture was extracted with ethyl acetate
7. 7
   SonstigeThe solvent was evaporated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (hexane)

Vorschrift

A solution of thieno[3,2-b]thiophene (see Fuller, L.; Iddon, B.; Smith, K. A. J. Chem. Soc. Perkin Trans 1 1997, 3465-3470) (1.27 g) in tetrahydrofuran (30 ml) was cooled to −78° C. under argon atmosphere, and thereto was added dropwise n-butyl lithium (1.59 M hexane solution, 5.70 ml). The mixture was stirred at 0° C. for 30 minutes, and cooled again to −78° C. Added thereto was a solution of hexachloroethane (2.14 g) in tetrahydrofuran (5 ml). The mixture was stirred at the same temperature for one hour, and warmed to 0° C. Added thereto was a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to give 2-Chlorothieno[3,2-b]thiophene (1.19 g) as a solid.

Quelle