Hydrochloric Acid → 6-Methoxy-2-naphthaleneboronic acid

A solution of n-butyl lithium in hexane (1.5M; 8.9 ml, 13.4 mmol) was added dropwise to a solution of 2-bromo-6-methoxynaphthalene (3.0 g, 12.7 mmol) in tetrahydrofuran (45 ml) under argon atmosphere at −60° C. and the mixture was stirred at the same temperature for 70 min. To the mixture was added tri-n-butylborate (5.2 ml, 19.0 mmol) and the mixture was stirred at the same temperature for 1 hr. and then at 5° C. for 1.5 hrs. To the reaction mixture was added dropwise 20% hydrochloric acid (13 ml) at 5° C., and water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure, and the residue was triturated with ethyl acetate and diethyl ether, filtered and dried to give (2-methoxy)-6-naphthalene boronic acid (1.50 g, 59%) as a colorless solid.

1. stirringthe mixture was stirred at the same temperature for 1 hr
2. waitand then at 5° C. for 1.5 hrs
3. extractionThe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with water and brine in turn
5. customdried
6. distillationThe solvent was distilled off under reduced pressure
7. customthe residue was triturated with ethyl acetate and diethyl ether
8. filtrationfiltered
9. customdried

ORD record

ord-ca504e7b04c24e9bb459ddab10f2f53f

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07345068B2