Reacción #803786

Ecuación de reacción

trimethyl borate

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

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

n-butyllithium

hydrochloric acid

→

light brown solid

Rendimiento 86.0%

9-phenyl-9H-carbazole-3-boronic acid

Rendimiento 86.0%

Disolventes

tetrahydrofuran

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISSOLUTIONwas dissolved
2. 2
   workup.STIRRINGthe solution was stirred for about 15 hours while the temperature of the solution
3. 3
   Temperaturawas being raised to room temperature
4. 4
   workup.STIRRINGthe solution was stirred for 1 hour
5. 5
   workup.STIRRINGAfter stirring
6. 6
   Otroan organic layer is separated from the mixture
7. 7
   Extracciónthe aqueous layer was extracted with ethyl acetate
8. 8
   Lavadowashed with saturated sodium bicarbonate
9. 9
   SecadoThe combined organic layer was dried with magnesium sulfate
10. 10
    FiltraciónAfter the drying, the mixture was subjected to gravity filtration
11. 11
    Otrocondensed
12. 12
    Otroto give an oily light brown substance
13. 13
    OtroThe obtained oily substance was dried under reduced pressure

Procedimiento

10 g (31 mmol) of 3-bromo-9-phenyl-9H-carbazole was put into a 500 mL three-neck flask, and The air in the flask was replaced with nitrogen. 150 mL of tetrahydrofuran (THF) was put into the flask, and 3-bromo-9-phenyl-9H-carbazole was dissolved therein. This solution was cooled down to −80° C. 20 mL (32 mmol) of n-butyllithium (a 1.58 mol/L hexane solution) was dropped into this solution with a syringe. After dropping, the solution was stirred at the same temperature for one hour. After the stirring, 3.8 mL (34 mmol) of trimethyl borate were added to the solution, and the solution was stirred for about 15 hours while the temperature of the solution was being raised to room temperature. After the stirring, about 150 mL (1.0 mol/L) of dilute hydrochloric acid was added to the solution, and then the solution was stirred for 1 hour. After stirring, an organic layer is separated from the mixture, the aqueous layer was extracted with ethyl acetate, and the extracted solution and the organic layer were combined and washed with saturated sodium bicarbonate. The combined organic layer was dried with magnesium sulfate. After the drying, the mixture was subjected to gravity filtration. The obtained filtrate was condensed to give an oily light brown substance. The obtained oily substance was dried under reduced pressure to give 7.5 g of a light brown solid, which was the object of the synthesis, in a yield of 86%. A synthesis scheme of Step 1 is shown by the following (a-1).

Fuente