Reaction #42185

Reaction equation

bromobenzene

diphenylamine

sodium-tert-butoxide

→

triphenylamine

Yield 85.0%

Solvents

xylene

Conditions

Workup

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

Procedure

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, 0.090 g (0.40 mmol) of palladium (II) acetate and 5 ml of xylene were weighed in the flask, followed by stirring. Further, 0.690 g (1.20 mmol) of n-butyldicyclohexylphosphonium tetraphenylborate obtained in Example B-47 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 8.345 g of triphenylamine (yield: 85 mol % based on diphenylamine). The melting point was 125-126° C.

Source