Reaktion #94244

Reaktionsgleichung

3,4-dibromo-butyronitrile

potassium carbonate

2-hydroxy-thiophenol

potassium carbonate

→

2-(1,4-benzoxathian-2-yl)-acetonitrile

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe starting material is prepared
2. 2
   workup.ADDITIONthe double addition procedure
3. 3
   workup.WAITafter a further 30 minutes said
4. 4
   TemperaturThe mixture is then refluxed for 20 hours
5. 5
   Temperaturcooled
6. 6
   Filtrationfiltered
7. 7
   Waschenthe residual salts washed with acetone
8. 8
   Sonstigethe filtrate evaporated
9. 9
   workup.DISTILLATIONThe residue is distilled (bulb to bulb)
10. 10
    Sonstigethe fraction boiling at 185°/0.5 mm Hg collected

Vorschrift

The starting material is prepared as follows: To the stirred, refluxing solution of 21 g of 2-hydroxy-thiophenol in 290 ml of acetone is added dropwise 12.5 g of 3,4-dibromo-butyronitrile along with small portions of 15.8 g of anhydrous potassium carbonate. After 30 minutes, the double addition procedure with said amounts of dibromo compound and potassium carbonate is repeated, and after a further 30 minutes said procedure is repeated a third time. The mixture is then refluxed for 20 hours, cooled, filtered, the residual salts washed with acetone, and the filtrate evaporated. The residue is distilled (bulb to bulb), and the fraction boiling at 185°/0.5 mm Hg collected, to yield the 2-(1,4-benzoxathian-2-yl)-acetonitrile.

Quelle