Reacción #737024

Ecuación de reacción

3-chloro-4-fluoro-nitrobenzene

Cylcohexanol

potassium hydride

→

desired product

2-Chloro-1-cyclohexyloxy-4-nitro-benzene

Disolventes

dimethylsulfoxide

diethyl ether

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting dark red colored solution is then heated for three hours to approximately 100 degrees
2. 2
   TemperaturaThe reaction mixture is then cooled
3. 3
   Lavadowashed successively with saturated aqueous ammonium chloride, three times with water
4. 4
   SecadoThe organic layer is then dried over anhydrous magnesium sulfate
5. 5
   Otrothe solvent is removed under reduced pressure
6. 6
   Otrothe resulting oil is chromatographed over silica gel (5% ethyl acetate in hexanes

Procedimiento

Cylcohexanol (2.9 g) in dimethylsulfoxide (20 mL) is added slowly to a flask containing potassium hydride (0.90 g, pre-washed three times with hexanes) under an atmosphere of argon and the solution is stirred for about 1 hour at room temperature. A solution of 3-chloro-4-fluoro-nitrobenzene (1 g) in dimethylsulfoxide (10 mL) is added and the resulting dark red colored solution is then heated for three hours to approximately 100 degrees. The reaction mixture is then cooled, diluted with diethyl ether (300 mL), and washed successively with saturated aqueous ammonium chloride, three times with water, then with saturated aqueous sodium chloride. The organic layer is then dried over anhydrous magnesium sulfate, the solvent is removed under reduced pressure, and the resulting oil is chromatographed over silica gel (5% ethyl acetate in hexanes is used as the eluant) to provide the desired product as an orange solid.

Fuente