反応 #531845

反応方程式

hydrochloric acid

9-(4-Bromophenyl)-10-phenylanthracene

n-butyllithium

trimethyl borate

→

4-(10-phenyl-9-anthryl)phenylboronic Acid

収率 84.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred for 24 hours at room temperature
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGthe mixture was stirred for 1 hour at room temperature
4. 4
   洗浄After that, an organic layer thereof was washed with water
5. 5
   その他separated into an organic layer
6. 6
   抽出a water layer, and the obtained water layer was further extracted with ethyl acetate
7. 7
   workup.ADDITIONThis extracted solution and the organic layer were mixed
8. 8
   洗浄washed with saturated aqueous solution, and magnesium sulfate
9. 9
   workup.ADDITIONwas added
10. 10
    その他so that moisture was removed
11. 11
    ろ過Then, suction filtration
12. 12
    その他was obtained
13. 13
    濃縮The obtained filtrate was concentrated
14. 14
    その他to provide a residue
15. 15
    その他The obtained residue was recrystallized with a mixed solution of chloroform and hexane, whereby 15 g of a powdery white solid of 4-(10-phenyl-9-anthryl)phenylboronic acid, which
16. 16
    その他the object of the synthesis
17. 17
    その他was obtained in a yield of 84% (synthesis scheme (a-5))

実験手順

In a 500 mL three-neck flask were stirred 20 g (49 mmol) of 9-(4-Bromophenyl)-10-phenylanthracene obtained by the above Steps 1(1) to 1(4) and 300 mL of tetrahydrofuran (abbreviation: THF) in a nitrogen atmosphere at −78° C. Then, 34 mL (54 mmol) of n-butyllithium (1.6 mol/L hexane solution) was dropped, and this mixture was stirred for 2 hours at the same temperature. After that, 13 mL (110 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. After that, an organic layer thereof was washed with water and separated into an organic layer and a water layer, and the obtained water layer was further extracted with ethyl acetate. This extracted solution and the organic layer were mixed and washed with saturated aqueous solution, and magnesium sulfate was added therein, so that moisture was removed. Then, suction filtration was performed so that a filtrate was obtained. The obtained filtrate was concentrated to provide a residue. The obtained residue was recrystallized with a mixed solution of chloroform and hexane, whereby 15 g of a powdery white solid of 4-(10-phenyl-9-anthryl)phenylboronic acid, which was the object of the synthesis, was obtained in a yield of 84% (synthesis scheme (a-5)).

出典