Reacción #80937

Ecuación de reacción

4-chlorophenol

5-chloro-2-nitrobenzonitrile

water

sodium hydroxide

→

2-nitro-5-(4-chlorophenoxy)benzonitrile

Rendimiento 52.6%

Disolventes

N,N-dimethylformamide

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoSodium hydride (60% in mineral oil), 1.5 grams (0.038 mole) was washed in petroleum ether
2. 2
   OtroThe petroleum ether was decanted
3. 3
   workup.ADDITIONUpon completion of addition
4. 4
   Temperaturathe reaction mixture was warmed
5. 5
   Temperaturato reflux where it
6. 6
   workup.STIRRINGstirred for about 18 hours
7. 7
   TemperaturaThe reaction mixture was then cooled
8. 8
   workup.STIRRINGThe mixture was stirred for about 15 minutes
9. 9
   FiltraciónThe resultant solid was collected by filtration
10. 10
    Otrorecrystallized from ethanol

Procedimiento

Sodium hydride (60% in mineral oil), 1.5 grams (0.038 mole) was washed in petroleum ether. The petroleum ether was decanted, and the sodium hydride was suspended in about 20 mL of N,N-dimethylformamide. The suspension was stirred, and solutions of 4.5 grams (0.035 mole) of 4-chlorophenol in 20 mL of N,N-dimethylformamide and 5.0 grams (0.027 mole) of 5-chloro-2-nitrobenzonitrile in 20 mL of N,N-dimethylformamide were added, respectively. Upon completion of addition, the reaction mixture was warmed to reflux where it stirred for about 18 hours. The reaction mixture was then cooled and poured into a mixture of 500 mL of water and 50 mL of aqueous 2N sodium hydroxide. The mixture was stirred for about 15 minutes, then it was allowed to stand for about 18 hours. The resultant solid was collected by filtration and recrystallized from ethanol, yielding 3.9 grams of 2-nitro-5-(4-chlorophenoxy)benzonitrile, mp 120°-122° C. The NMR spectrum was consistent with the proposed structure.

Fuente