Réaction #94088

Équation de réaction

hydrochloric acid

thioanisole

n-butyllithium

dimethyldisulphide

→

title compound

Phenylthio-methylthio-methane

Solvants

tetrahydrofuran

n-hexane

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   LavageThe extracts were washed with water
3. 3
   Concentrationan aqueous solution of sodium chloride and concentrated under reduced pressure
4. 4
   workup.DISTILLATIONThe residue was purified by distillation in vacuo
5. 5
   Autreto give 18.0 g

Mode opératoire

120 ml. of a 1.3M n-butyllithium solution in n-hexane were added dropwise to a solution of 18.8 ml. of thioanisole in 240 ml. of tetrahydrofuran at -20° C. and the reaction mixture was stirred at that temperature for 2 hours. After cooling to -70° C., 16.4 g. of dimethyldisulphide were added to the reaction mixture, which was then stirred at -70° C. for 15 minutes and at room temperature for 1 hour. The reaction mixture was poured into dilute aqueous hydrochloric acid and extracted with ethyl acetate. The extracts were washed with water and an aqueous solution of sodium chloride and concentrated under reduced pressure. The residue was purified by distillation in vacuo to give 18.0 g. of the title compound having the following physical characteristics:

Source