Reaktion #353627

Reaktionsgleichung

potassium t-butoxide

chloromethyl phenyl sulfide

4-bromosaccharin

→

4-bromo-2-phenylthiomethylsaccharin

Ausbeute 84.0%

Lösungsmittel

toluene

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux under a nitrogen atmosphere for eight hours
2. 2
   workup.WAITat ambient temperature for about sixteen hours
3. 3
   TemperaturThe reaction mixture was then cooled
4. 4
   Waschenthe organic layer washed with bicarbonate, water and brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigeThe residual solid was recrystallized from toluene-hexane

Vorschrift

A mixture of 3.27 g (0.012 mol) of 4-bromosaccharin [Japanese Pat. Publcn. 58/79,034, published May 12, 1983; C. A. 100, 7773w (1984)], 1.63 g (0.015 mol) of potassium t-butoxide, 0.39 g (0.0012 mol) of tetrabutylammonium bromide and 3.0 ml (0.022 mol) of chloromethyl phenyl sulfide in 100 ml of toluene was heated under reflux under a nitrogen atmosphere for eight hours and then at ambient temperature for about sixteen hours. The reaction mixture was then cooled, diluted with ethyl acetate and the organic layer washed with bicarbonate, water and brine and then dried over magnesium sulfate and taken to dryness in vacuo. The residual solid was recrystallized from toluene-hexane to give 3.86 g (84%) of 4-bromo-2-phenylthiomethylsaccharin, mp 174.5°-178° C.

Quelle