Reaktion #75707

Reaktionsgleichung

3-Bromo-4-methylthiobenzoic acid methyl ester

1-ethoxyvinyl tributyl tin

water

hydrochloric acid

→

3-acetyl-4-methylthiobenzoic acid methyl ester

Lösungsmittel

dioxan

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   SonstigeSolvent was removed at reduced pressure
3. 3
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate
4. 4
   Filtrationfiltered through celite
5. 5
   SonstigeThe filtrate was evaporated to dryness
6. 6
   Sonstigethe residue triturated with hexane

Vorschrift

3-Bromo-4-methylthiobenzoic acid methyl ester (0.86 g), 1-ethoxyvinyl tributyl tin (1.39 ml) and tetrakis triphenylphosphinepalladium (IV) (0.15 g) were combined in dioxan (50 ml) and boiled for 24 h. The mixture was cooled, water (10 ml) and conc. hydrochloric acid (1 ml) added and the mixture stirred at room temperature overnight. Solvent was removed at reduced pressure, the residue dissolved in ethyl acetate and filtered through celite. The filtrate was evaporated to dryness and the residue triturated with hexane to give 3-acetyl-4-methylthiobenzoic acid methyl ester (0.45 g) as a yellow solid. m/z (API+): 225 (MH+).

Quelle