反応 #531847

反応方程式

hydrochloric acid

3-bromo-9-phenylcarbazole

n-butyllithium

trimethyl borate

→

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

収率 80.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他obtained by the above Step 3
2. 2
   その他to 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
   洗浄This 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
   その他was removed
9. 9
   ろ過This suspending solution was filtered
10. 10
    濃縮the obtained filtrate was concentrated
11. 11
    workup.ADDITIONThen, chloroform and hexane were added
12. 12
    その他recrystallization
13. 13
    その他the object of the synthesis
14. 14
    その他was obtained in a yield of 80% (synthesis scheme (b-1))

実験手順

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)).

出典