Reaktion #367296

Reaktionsgleichung

water

N-phthalimidopyrrole

o-fluorobenzoyl chloride

→

solid

Ausbeute 19.1%

2-(2-Fluorobenzoyl)-1-phthalimidopyrrole

Ausbeute 19.1%

Lösungsmittel

dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThereafter, it was cooled
2. 2
   Extraktionextracted with dichloromethane
3. 3
   ExtraktionThe organic extract
4. 4
   Waschenwas washed with water and with saturated sodium chloride solution
5. 5
   Trocknendried over magnesium sulfate
6. 6
   FiltrationThe solution was filtered
7. 7
   Sonstigeevaporated to an oil which
8. 8
   Sonstigeyielded a solid upon trituration with ethanol (yield 11 g, m.p. 180°-190°)
9. 9
   SonstigeThis material was purified by column chromatography (silica gel, dichloromethane)

Vorschrift

To a mixture of N-phthalimidopyrrole (10 g, 47 mmole) and fused zinc chloride (10 g, 73 mmole) in 80 ml dichloroethane was added o-fluorobenzoyl chloride (7.5 g, 47 mmole). The reaction mixture was stirred at ambient temperature for twenty hours and at 80° for one hour. Thereafter, it was cooled, poured into water and extracted with dichloromethane. The organic extract was washed with water and with saturated sodium chloride solution, and dried over magnesium sulfate. The solution was filtered and evaporated to an oil which yielded a solid upon trituration with ethanol (yield 11 g, m.p. 180°-190°). This material was purified by column chromatography (silica gel, dichloromethane) to give 3 g solid. This material was recrystallized from isopropanol to give 2.6 g (17%) crystals, m.p. 202°-203°.

Quelle