Reacción #50900

Ecuación de reacción

1,5-Diaminonaphthalene

tri-t-butylphosphine

sodium t-butoxide

bromobenzene

→

N,N,N′-triphenyl-1,5-diaminonaphthalene

Rendimiento 15.0%

Disolventes

xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter heating for another 6 h
2. 2
   TemperaturaAfter heating for another 15 h the heat
3. 3
   Otrowas removed
4. 4
   TemperaturaAfter cooling to room temperature
5. 5
   Filtraciónthe solid present was filtered off
6. 6
   Otrothe filtrate was purified by column chromatography

Procedimiento

1,5-Diaminonaphthalene (16.0 g, 0.101 mol) was combined with bromobenzene (47.1 g, 0.300 mol), palladium diacetate (1.2 g, 0.004 mol), tri-t-butylphosphine (4 mL), sodium t-butoxide (24.0 g, 0.26 mol), and xylene (400 mL). The mixture was heated at 140° C. with magnetic stirring under a nitrogen atmosphere. After 15 h, an additional amount of palladium diacetate (0.100 g, 0.0004 mol) was added. After heating for another 6 h, an additional amount of palladium diacetate (0.100 g, 0.0004 mol) was added. After heating for another 15 h the heat was removed. After cooling to room temperature, the solid present was filtered off and the filtrate was purified by column chromatography. This afforded 6.0 g (15% yield) of N,N,N′-triphenyl-1,5-diaminonaphthalene.

Fuente