Réaction #42187

Équation de réaction

bromobenzene

diphenylamine

sodium-tert-butoxide

→

triphenylamine

Rendement 87.0%

Solvants

xylene

Conditions de réaction

Traitement

1. 1
   AutreA 100-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   AutreThe flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 125° C. for 4 hours
5. 5
   AutreAfter the completion of the reaction, 45 ml of xylene and 50 ml of saturated sodium chloride solution
6. 6
   workup.ADDITIONwere added
7. 7
   Autrefollowed by separation
8. 8
   AutreThe organic phase was purified by column chromatography

Mode opératoire

A 100-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 7.536 g (48 mmol) of bromobenzene, 6.769 g (40 mmol) of diphenylamine, 4.613 g (48 mmol) of sodium-tert-butoxide, 0.009 g (0.04 mmol) of palladium (II) acetate and 5 ml of xylene were weighed in the flask, followed by stirring. Further, 0.074 g (0.12 mmol) of 2-biphenylyl-di-tert-butylphosphonium tetraphenylborate obtained in Example B-10 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 125° C. for 4 hours. After the completion of the reaction, 45 ml of xylene and 50 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 8.537 g of triphenylamine (yield: 87 mol % based on diphenylamine). The melting point was 125-126° C.

Source