反応 #60237

反応方程式

hydrochloric acid

triisopropyl borate

normal butyllithium

4-bromotriphenylamine

→

triphenylamine-4-boronic acid

収率 70.6%

溶媒

ether

hexane

toluene

ethyl ether

反応条件

後処理

1. 1
   温度The 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
   その他the aqueous layer was removed
5. 5
   その他The organic layer was dried on magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   その他The solid matter thus obtained
8. 8
   洗浄was washed with hexane and toluene

実験手順

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.

出典