Réaction #167471

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.STIRRINGthis mixture was stirred for 2 hours at the same temperature
2. 2
   workup.STIRRINGthe mixture was stirred for 24 hours at room temperature
3. 3
   Autrewas brought back to room temperature
4. 4
   workup.STIRRINGthis mixture was stirred for 1 hour
5. 5
   LavageAfter that, the organic layer thereof was washed with water
6. 6
   Autreseparated into the organic layer
7. 7
   Extractionthe aqueous layer, and the obtained aqueous layer was extracted with ethyl acetate
8. 8
   LavageAfter this extracted solution was washed together with the organic layer with saturated saline, magnesium sulfate
9. 9
   workup.ADDITIONwas added
10. 10
    Autrefor drying
11. 11
    FiltrationThe mixture was subjected to suction filtration
12. 12
    Concentrationthe obtained filtrate was concentrated
13. 13
    Autreto obtain a solid
14. 14
    AutreThe obtained solid was recrystallized from a mixed solvent of chloroform and hexane, whereby 15 g of a white powdered solid of 4-(10-phenyl-9-anthryl)phenylboronic acid, which
15. 15
    Autrethe object of the synthesis
16. 16
    Autrewas obtained in a yield of 84% (synthesis scheme (X-5))

Mode opératoire

In a 500 mL three-neck flask were added 20 g (49 mmol) of 9-(4-bromophenyl)-10-phenylanthracene obtained by the above Steps 1(1) to 1(4) of Synthesis Example 3 and 300 mL of tetrahydrofuran (abbr.: THF), and the mixture was stirred under a nitrogen stream 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 the stirring, 13 mL (110 mmol) of trimethyl borate was added to this solution, and the mixture was stirred for 24 hours at room temperature. After the stirring, this mixture was brought back to room temperature, 200 mL of (1.0 mol/L) hydrochloric acid was added therein, and this mixture was stirred for 1 hour. After that, the organic layer thereof was washed with water and separated into the organic layer and the aqueous layer, and the obtained aqueous layer was extracted with ethyl acetate. After this extracted solution was washed together with the organic layer with saturated saline, magnesium sulfate was added therein for drying. The mixture was subjected to suction filtration, and the obtained filtrate was concentrated to obtain a solid. The obtained solid was recrystallized from a mixed solvent of chloroform and hexane, whereby 15 g of a white powdered 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 (X-5)).

Source