Reaktion #60237

Reaktionsgleichung

hydrochloric acid

triisopropyl borate

normal butyllithium

4-bromotriphenylamine

→

triphenylamine-4-boronic acid

Ausbeute 70.6%

Lösungsmittel

ether

hexane

toluene

ethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe 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
   Sonstigethe aqueous layer was removed
5. 5
   SonstigeThe organic layer was dried on magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off
7. 7
   SonstigeThe solid matter thus obtained
8. 8
   Waschenwas washed with hexane and toluene

Vorschrift

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.

Quelle