Reacción #1182197

Ecuación de reacción

hydrochloric acid

3-bromo-9-phenyl-9H-carbazole

n-butyllithium

trimethyl borate

→

light brown powder

Rendimiento 68.0%

9-phenyl-9H-carbazol-3-boronic acid

Rendimiento 68.0%

Disolventes

tetrahydrofuran

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe solution was stirred for about 15 hours while the temperature of the solution
2. 2
   Temperaturawas being increased to room temperature
3. 3
   workup.STIRRINGthe solution was stirred for 1 hour
4. 4
   ExtracciónAfter the stirring, the aqueous layer of the mixture was extracted with ether acetate
5. 5
   Lavadowashed with a saturated sodium hydrogen carbonate solution
6. 6
   SecadoThe organic layer was dried with magnesium sulfate
7. 7
   FiltraciónAfter the drying, this mixture was subjected to gravity filtration
8. 8
   Otrocondensed
9. 9
   Otroto give an oily light brown substance
10. 10
    OtroThe obtained oily substance was recrystallized with chloroform/hexane

Procedimiento

10 g (32 mmol) of 3-bromo-9-phenyl-9H-carbazole was put into a 500 mL three-neck flask. The air in the flask was replaced with nitrogen. To the mixture were added 150 mL of tetrahydrofuran (THF), and then the solution was cooled to −80° C. Into this solution, 22 mL (36 mmol) of n-butyllithium (a 1.61 mol/L hexane solution) was dropped by a syringe. After the dropping was completed, this solution was stirred at the same temperature for 1 hour. After the stirring, 4.6 mL, (40 mmol) of trimethyl borate was added to the solution, and the solution was stirred for about 15 hours while the temperature of the solution was being increased to room temperature. Thereafter, to the solution was added about 50 mL (1.0 mol/L) of dilute hydrochloric acid, and then the solution was stirred for 1 hour. After the stirring, the aqueous layer of the mixture was extracted with ether acetate. The extract was combined with the organic layer and then washed with a saturated sodium hydrogen carbonate solution. The organic layer was dried with magnesium sulfate. After the drying, this mixture was subjected to gravity filtration. The obtained filtrate was condensed to give an oily light brown substance. The obtained oily substance was recrystallized with chloroform/hexane to give 6.2 g of a light brown powder, which was the object of the synthesis, at a yield of 68%. A synthesis scheme of Step 1 is shown in (d-1) given below.

Fuente