Reacción #77407

Ecuación de reacción

3-methoxyphenylboronic acid

5-bromo-2-fluoronitrobenzene

sodium carbonate

→

4-fluoro-3′-methoxy-3-nitrobiphenyl

Rendimiento 77.0%

Disolventes

water

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturato reflux for 2 hours
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe ethyl acetate was washed with saturated sodium bicarbonate, brine
5. 5
   Otrodried
6. 6
   Concentraciónconcentrated
7. 7
   Otroto give an oily solid
8. 8
   OtroThe solid was purified by column chromatography on silica gel in ethyl acetate:hexane 1:6

Procedimiento

Tetrakis(triphenylphosphine)palladium (0.7 g) was added to a mixture of 3.8 g of 3-methoxyphenylboronic acid, 5 g of 5-bromo-2-fluoronitrobenzene and 11 mL of 2M sodium carbonate solution in 100 mL of toluene. The mixture was heated to reflux for 2 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate was washed with saturated sodium bicarbonate, brine, dried, and concentrated to give an oily solid. The solid was purified by column chromatography on silica gel in ethyl acetate:hexane 1:6 to give 4.3 g (77% yield) of 4-fluoro-3′-methoxy-3-nitrobiphenyl.

Fuente