Reaktion #49735

Reaktionsgleichung

cyclopropanecarbonyl chloride

n-Butyllithium

1-bromo-2-[2-(methylsulphenyl)-4-trifluoromethylphenyl]acetylene

1,1-dibromo-2-[2-(methylsulphenyl)-4-trifluoromethylphenyl]ethene

ammonium chloride

→

3-cyclopropyl-1-[2-(methylsulphenyl)-4-trifluoromethylphenyl]prop-1-yn-3-one

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintaining the temperature below -70° C
2. 2
   Sonstigeto rise to room temperature
3. 3
   workup.STIRRINGthe mixture was stirred for 2 hours
4. 4
   Extraktionthe mixture was extracted with ether
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   SonstigeThe flitrate was evaporated to dryness
8. 8
   Sonstigethe residue was purified by chromotography
9. 9
   Wascheneluted with a mixture of hexane and ether

Vorschrift

n-Butyllithium (2.5M, 1.45 ml) was added to a stirred cooled solution of 1-bromo-2-[2-(methylsulphenyl)-4-trifluoromethylphenyl]acetylene and 1,1-dibromo-2-[2-(methylsulphenyl)-4-trifluoromethylphenyl]ethene (1.0 g) in THF, maintaining the temperature below -70° C. The mixture was stirred for 30 minutes and cyclopropanecarbonyl chloride (0.75 g) was added. The temperature was allowed to rise to room temperature and the mixture was stirred for 2 hours, aqueous ammonium chloride was added and the mixture was extracted with ether, dried (MgSO4) and filtered. The flitrate was evaporated to dryness and the residue was purified by chromotography eluted with a mixture of hexane and ether to give 3-cyclopropyl-1-[2-(methylsulphenyl)-4-trifluoromethylphenyl]prop-1-yn-3-one (0.64 g) as yellow oil, NMR (CDCI3) 1.15(m,2H), 1.45(m,2H), 2.2(m,1H), 2.6(s,1H), 7.35(d,1H) 7.4(s,1H), 7.6(d,1H).

Quelle