Reaction #531847

Reaction equation

hydrochloric acid

3-bromo-9-phenylcarbazole

n-butyllithium

trimethyl borate

→

9-phenyl-9H-carbazol-3-boronic Acid

Yield 80.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherobtained by the above Step 3
2. 2
   Otherto provide a solution
3. 3
   workup.STIRRINGthe mixture was stirred for 24 hours at room temperature
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGthe mixture was stirred for 1 hour at room temperature
6. 6
   WashThis mixture was washed with water, aqueous sodium hydroxide, and water in this order, and magnesium sulfate
7. 7
   workup.ADDITIONwas added so that the moisture
8. 8
   Otherwas removed
9. 9
   FiltrationThis suspending solution was filtered
10. 10
    Concentrationthe obtained filtrate was concentrated
11. 11
    workup.ADDITIONThen, chloroform and hexane were added
12. 12
    Otherrecrystallization
13. 13
    Otherthe object of the synthesis
14. 14
    Otherwas obtained in a yield of 80% (synthesis scheme (b-1))

Procedure

In a 500 mL three-neck flask were stirred 29 g (90 mmol) of 3-bromo-9-phenylcarbazole obtained by the above Step 3 described in Synthesis Example 1 and 200 mL of tetrahydrofuran (abbreviation: THF) at −78° C. to provide a solution. Then, 10 mL (69 mmol) of n-butyllithium (1.6 mol/L hexane solution) was dropped therein, and the mixture was stirred for 2 hours at the same temperature. Furthermore, 13 mL (140 mmol) of trimethyl borate was added therein, and the mixture was stirred for 24 hours at room temperature. After the reaction, 200 mL of 1.0 mol/L hydrochloric acid was added therein, and the mixture was stirred for 1 hour at room temperature. This mixture was washed with water, aqueous sodium hydroxide, and water in this order, and magnesium sulfate was added so that the moisture was removed. This suspending solution was filtered and the obtained filtrate was concentrated. Then, chloroform and hexane were added therein, ultrasonic waves were applied thereto, and then recrystallization thereof was performed. Accordingly, 21 g of a powdery white solid of 9-phenyl-9H-carbazol-3-boronic acid, which was the object of the synthesis, was obtained in a yield of 80% (synthesis scheme (b-1)).

Source