반응 #60237

반응 방정식

hydrochloric acid

triisopropyl borate

normal butyllithium

4-bromotriphenylamine

→

triphenylamine-4-boronic acid

수율 70.6%

용매

ether

hexane

toluene

ethyl ether

반응 조건

후처리

1. 1
   온도The reaction solution was cooled down again to −78° C.
2. 2
   workup.STIRRINGThe reaction solution was stirred at room temperature for 5 hours
3. 3
   workup.STIRRINGstirred for one hour
4. 4
   기타the aqueous layer was removed
5. 5
   기타The organic layer was dried on magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   기타The solid matter thus obtained
8. 8
   세척was washed with hexane and toluene

실험 절차

A dry ethyl ether 100 ml and dry toluene 100 ml solution of 4-bromotriphenylamine 16.2 g was cooled down to −78° C. under argon atmosphere, and a hexane solution 32.8 ml of 1.6M normal butyllithium was dropwise added thereto. The reaction solution was stirred for one hour while heating up to 0° C. The reaction solution was cooled down again to −78° C., and a dry ether 50 ml solution of triisopropyl borate 23.5 g was dropwise added thereto. The reaction solution was stirred at room temperature for 5 hours. 1N hydrochloric acid 100 ml was added thereto and stirred for one hour, and then the aqueous layer was removed. The organic layer was dried on magnesium sulfate, and the solvent was distilled off. The solid matter thus obtained was washed with hexane and toluene to obtain 10.2 g of triphenylamine-4-boronic acid.

출처