Reacción #2304293

Ecuación de reacción

4-benzyloxybromobenzene

4-(trifluoromethoxy)benzeneboronic acid

sodium carbonate

ethylene glycol dimethyl ether

→

4-benzyloxy-4′-(trifluoromethoxy)biphenyl

Rendimiento 35.9%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe reaction mixture was extracted with toluene
2. 2
   Secadothe organic layer was dried with anhydrous magnesium sulfate
3. 3
   OtroThe solvent was evaporated away
4. 4
   Otrothe resulting residue was purified through silica gel chromatography (elution solvent: heptane/toluene=7/3)
5. 5
   Otrorecrystallized from heptane

Procedimiento

A reaction mixture comprising 6.7 g of 4-benzyloxybromobenzene, 5.0 g of 4-(trifluoromethoxy)benzeneboronic acid, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 5.1 g of sodium carbonate, 100 ml of ethylene glycol dimethyl ether and 20 ml of pure water was refluxed for 5 hours. The reaction mixture was extracted with toluene, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was purified through silica gel chromatography (elution solvent: heptane/toluene=7/3) and recrystallized from heptane, and 3.0 g of 4-benzyloxy-4′-(trifluoromethoxy)biphenyl was obtained. m.p.: 136-137.2° C.

Fuente