Réaction #531845

Équation de réaction

hydrochloric acid

9-(4-Bromophenyl)-10-phenylanthracene

n-butyllithium

trimethyl borate

→

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

Rendement 84.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

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
   LavageAfter that, an organic layer thereof was washed with water
5. 5
   Autreseparated into an organic layer
6. 6
   Extractiona 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
   Lavagewashed with saturated aqueous solution, and magnesium sulfate
9. 9
   workup.ADDITIONwas added
10. 10
    Autreso that moisture was removed
11. 11
    FiltrationThen, suction filtration
12. 12
    Autrewas obtained
13. 13
    ConcentrationThe obtained filtrate was concentrated
14. 14
    Autreto provide a residue
15. 15
    AutreThe 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
    Autrethe object of the synthesis
17. 17
    Autrewas obtained in a yield of 84% (synthesis scheme (a-5))

Mode opératoire

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)).

Source