Reaktion #2063595

Reaktionsgleichung

4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonic acid sodium salt

phosphorous pentachloride

→

4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonyl chloride

Ausbeute 17.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction warmed to 40°
2. 2
   workup.DISSOLUTIONfollowed by dissolution of the reagents
3. 3
   SonstigeThe reaction was then quenched with ice
4. 4
   Extraktionextracted with dichloromethane
5. 5
   Waschenwashed with water, brine
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe resulting oil was purified via flash chromatography

Vorschrift

To a solution of the crude 4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonic acid sodium salt (2.81 g, 8.7 mmol) was added 2.8 g of phosphorous pentachloride and 50 mL of dichloromethane. The reaction warmed to 40° followed by dissolution of the reagents. The reaction was then quenched with ice, extracted with dichloromethane, washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was purified via flash chromatography using 20:1 Hex:EtOAc to afford 0.5 g (17%) of 4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonyl chloride.

Quelle