Reaktion #516154

Reaktionsgleichung

2-hydroxy-2-(3-nitrophenyl)acetonitrile

pyridine

thionyl chloride

→

title compound

Ausbeute 89.0%

2-Chloro-2-(3-nitrophenyl)acetonitrile

Ausbeute 89.0%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was gently heated
2. 2
   Temperaturunder reflux and after 30 min the solvent
3. 3
   Sonstigewas removed by evaporation
4. 4
   Sonstigeto give a pale yellow solid
5. 5
   SonstigeThis was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (3:1

Vorschrift

A solution of 2-hydroxy-2-(3-nitrophenyl)acetonitrile (Preparation 113, 1.0 g, 5.62 mmol) in diethyl ether (10 ml) was stirred at room temperature and treated with pyridine (0.1 ml, 1.24 mmol) followed by thionyl chloride (0.82 ml, 11.2 mmol) dropwise over 5 minutes. The mixture was gently heated under reflux and after 30 min the solvent was removed by evaporation to give a pale yellow solid. This was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (3:1 and then 2:1) to give the title compound as a white crystalline solid (980 mg, 89%).

Quelle