Reaktion #157745

Reaktionsgleichung

Potassium t-butoxide

bromocyclopropane

2-methylbenzenethiol

→

1-(cyclopropylsulfanyl)-2-methylbenzene

Lösungsmittel

dimethyl sulfoxide

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was cooled to room temperature
2. 2
   Extraktionfollowed by extraction with ethyl acetate
3. 3
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   SonstigeThe solvent was then evaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Vorschrift

Potassium t-butoxide (994 mg) and bromocyclopropane (2.92 g) were added to a solution of 2-methylbenzenethiol (1.05 g) in dimethyl sulfoxide (10 mL), and the mixture was stirred at 100° C. for 9.5 hours. The reaction solution was cooled to room temperature and brine was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 1-(cyclopropylsulfanyl)-2-methylbenzene as an orange oil (1.41 g, quant.).

Quelle