Reacción #352937

Ecuación de reacción

potassium hydroxide

p-iodotoluene

p-bromoaniline

1,10-phenanthroline

→

desired product

Bis(p-methylphenyl)-p-bromophenylamine

Disolventes

xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a 500 milliliter three-necked flask equipped with a mechanical stirrer
2. 2
   workup.ADDITIONwere added
3. 3
   Otrowas then adjusted to 125° C.
4. 4
   Otrothe reaction
5. 5
   Otrocomplete at 2 hours
6. 6
   Otrothe reaction was terminated
7. 7
   workup.ADDITIONby adding 24 grams of acetic acid
8. 8
   Otropartitioning the reaction mixture between 100 grams of toluene and 100 grams of deionized water
9. 9
   Otrothe solvent removed

Procedimiento

In a 500 milliliter three-necked flask equipped with a mechanical stirrer, thermometer and Dean-Stark trap, all under an argon atmosphere, were added molten p-iodotoluene (27.3 grams, 125 millimoles), 22 grams of xylene, p-bromoaniline (8.7 grams, 50 millimoles), and 1,10-phenanthroline (1.8 grams, 10 millimoles). The reaction mixture was then heated to 100° C. at which point potassium hydroxide flake (22.4 grams, 400 millimoles) and cuprous chloride (1 gram, 10 millimoles) were added. The temperature was then adjusted to 125° C., and the reaction progress monitored by high performance liquid chromatography. Analysis showed the reaction to be 94 percent complete at 2 hours and 98 percent complete at 5 hours at which point the reaction was terminated. Product isolation was accomplished by adding 24 grams of acetic acid, and partitioning the reaction mixture between 100 grams of toluene and 100 grams of deionized water. The organic phase was further washed several times with deionized water, and the solvent removed to afford 15 grams (84.5 percent) of the desired product of high purity (HPLC, 98 area percent).

Fuente