Ammonium Chloride → 2-Benzyloxy-1-methoxybenzeneboronic acid

Temperature

-78 °C

4.86 g of 2-Benzyloxy-4-bromo-1-methoxybenzene was dissolved in 100 ml of anhydrous tetrahydrofuran and cooled to −78° C. in a nitrogen atmosphere. 15 ml of 1.6 M n-butyl lithium in hexane was added dropwise, and the mixture was stirred for 30 minutes. 6 ml of Triisopropoxy borate was added all at once, and the mixture was allowed to warm overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was dissolved in 1N aqueous sodium hydroxide and extracted with diethyl ether. The aqueous layer was neutralized with 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated to give 1.76 of the title compound.

1. temperatureto warm overnight at room temperature
2. extractionwas then extracted with ethyl acetate
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationthe filtrate was concentrated
6. dissolutionThe residue was dissolved in 1N aqueous sodium hydroxide
7. extractionextracted with diethyl ether
8. extractionextracted with ethyl acetate
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationthe filtrate was concentrated

ORD record

ord-4a6fe16e71db4bb9aadec937a1c77734

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687664B2