Reacción #531845

Ecuación de reacción

hydrochloric acid

9-(4-Bromophenyl)-10-phenylanthracene

n-butyllithium

trimethyl borate

→

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

Rendimiento 84.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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
   LavadoAfter that, an organic layer thereof was washed with water
5. 5
   Otroseparated into an organic layer
6. 6
   Extraccióna 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
   Lavadowashed with saturated aqueous solution, and magnesium sulfate
9. 9
   workup.ADDITIONwas added
10. 10
    Otroso that moisture was removed
11. 11
    FiltraciónThen, suction filtration
12. 12
    Otrowas obtained
13. 13
    ConcentraciónThe obtained filtrate was concentrated
14. 14
    Otroto provide a residue
15. 15
    OtroThe 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
    Otrothe object of the synthesis
17. 17
    Otrowas obtained in a yield of 84% (synthesis scheme (a-5))

Procedimiento

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)).

Fuente