Reaktion #70059

Reaktionsgleichung

hydrochloric acid

4-bromotriphenylamine

n-butyllithium

trimethyl borate

→

white powdered solid

Ausbeute 59.9%

N,N-diphenylanilin-4-boronic acid

Ausbeute 59.9%

Lösungsmittel

tetrahydrofuran

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter the dropping, this solution was stirred at the same temperature for 1 hour
2. 2
   workup.STIRRINGthe solution was stirred for 1 hour while the temperature of the solution
3. 3
   Temperaturwas being increased to room temperature
4. 4
   workup.STIRRINGthe solution was stirred for about 15 hours
5. 5
   WaschenThe organic layer was washed with a saturated sodium hydrogen carbonate solution
6. 6
   TrocknenThen, the organic layer was dried with magnesium sulfate
7. 7
   FiltrationThis mixture was subjected to gravity filtration
8. 8
   Sonstigecondensed
9. 9
   Sonstigeto give a white solid
10. 10
    SonstigeThe obtained solid was recrystallized with chloroform/hexane

Vorschrift

10 g (30 mmol) of 4-bromotriphenylamine was put into a 500 mL three-neck flask. The air in the flask was replaced with nitrogen. To the mixture were added 20 mL of tetrahydrofuran (THF), and then the mixture was stirred at −80° C. Into this solution, 20 mL (32 mmol) of n-butyllithium (a 1.6 mol/L hexane solution) was dropped by a syringe. After the dropping, this solution was stirred at the same temperature for 1 hour. After the stirring, 40 mL (60 mmol) of trimethyl borate was added to the solution, and the solution was stirred for 1 hour while the temperature of the solution was being increased to room temperature. To the solution was added 200 mL (1.0 mol/L) of hydrochloric acid, and then the solution was stirred for about 15 hours. The organic layer was washed with a saturated sodium hydrogen carbonate solution and then a saturated saline solution. Then, the organic layer was dried with magnesium sulfate. This mixture was subjected to gravity filtration. The obtained filtrate was condensed to give a white solid. The obtained solid was recrystallized with chloroform/hexane to give 5.2 g of a white powdered solid, which was the object of the synthesis, at a yield of 58%. A synthesis scheme of Step 2 is shown in (c-2) given below.

Quelle