Reaction #531845

Reaction equation

hydrochloric acid

9-(4-Bromophenyl)-10-phenylanthracene

n-butyllithium

trimethyl borate

→

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

Yield 84.0%

Solvents

tetrahydrofuran

Conditions

Workup

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
   WashAfter that, an organic layer thereof was washed with water
5. 5
   Otherseparated 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
   Washwashed with saturated aqueous solution, and magnesium sulfate
9. 9
   workup.ADDITIONwas added
10. 10
    Otherso that moisture was removed
11. 11
    FiltrationThen, suction filtration
12. 12
    Otherwas obtained
13. 13
    ConcentrationThe obtained filtrate was concentrated
14. 14
    Otherto provide a residue
15. 15
    OtherThe 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
    Otherthe object of the synthesis
17. 17
    Otherwas obtained in a yield of 84% (synthesis scheme (a-5))

Procedure

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