Hydrochloric Acid → (4-Methoxy-2-phenylphenyl)boronic acid

Temperature

0 °C

An excess of 1.6M n-BuLi in hexane (50 mL, 80 mmol) was added to a solution of 2-bromo-5-methoxybiphenyl (19.1 g, 72.7 mmol) in 350 ml dry tetrahydrofuran at −78° C. under N2. The reaction mixture was then maintained at 0° C. for 1 h before cooling to −78° C., trimethylborate (10.4 g, 100 mmol) was added dropwise, the solution was then warmed slowly to room temperature and stirred for 24 h. 2N HCl (150 ml) was added and then the mixture was stirred for a further 1 h. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum, and the residue was crystallized from n-hexane to give 9.5 g of the 5-methoxybiphenyl-2-ylboronic acid as a white solid (57%).

1. temperaturebefore cooling to −78° C.
2. temperaturethe solution was then warmed slowly to room temperature
3. stirringthe mixture was stirred for a further 1 h
4. extractionThe reaction mixture was extracted with ethyl acetate and water
5. dry with materialdried with anhydrous magnesium sulfate
6. customthe solvent was evaporated in vacuum
7. customthe residue was crystallized from n-hexane

ORD record

ord-4b2700bdea3e40a79e934d621b51ca38

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09166177B2