Reacción #75934

Ecuación de reacción

hydrogen peroxide

4-Methoxy-benzeneboronic acid

4-(4-bromo-phenyl)-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole

sodium carbonate

→

solid

Rendimiento 82.2%

4-(4′-Methoxy-biphenyl-4-yl)-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole

Rendimiento 82.2%

Disolventes

water

ethyl alcohol

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was refluxed for 12 hours
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   SecadoThe organic extracts were dried over MgSO4
4. 4
   OtroEvaporation and crystallization from hexanes/ethyl ether

Procedimiento

4-Methoxy-benzeneboronic acid (1.44 g, 7.19 mmol) in ethyl alcohol (5 mL) was added into a mixture of 4-(4-bromo-phenyl)-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole (2.5 g, 6.54 mmol), sodium carbonate (2N, 6.5 mL), tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.196 mmol), and toluene (200 mL). The reaction mixture was refluxed for 12 hours, cooled to room temperature, and treated with hydrogen peroxide (30%, 5 mL) for 1 hour. Then, the mixture was poured into water and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and crystallization from hexanes/ethyl ether gave a white solid (2.2 g, 82% yield): mp 167-168° C.; MS m/e 409 (M+);

Fuente