Hydrochloric Acid → (1-Phenylvinyl)boronic acid

Temperature

-78 °C

A solution of α-bromo styrene (5.5 g, 30 mmol) in diethyl ether (30 mL) at −78° C. was treated with a solution of tert-BuLi (1.7 M solution, 21.2 mL, 36 mmol), stirred at −78° C. for 0.5 hours, treated with triisopropyl borate (8.31 mL, 36 mmol) over 48 minutes, stirred for 1 hour, warmed to room temperature over 18 hours, diluted with diethyl ether (100 mL), treated with 1M HCl (100 mL), stirred at room temperature for 5 hours, concentrated to remove the THF, adjusted pH 14 with IN NaOH, washed with hexane, adjusted to pH 1 with 1M HCl, and extracted with ethyl acetate. The extract was dried (Na2SO4), filtered and concentrated to provide the title compound.

1. stirringstirred for 1 hour
2. temperaturewarmed to room temperature over 18 hours
3. stirringstirred at room temperature for 5 hours
4. concentrationconcentrated
5. customto remove the THF, adjusted pH 14 with IN NaOH
6. washwashed with hexane
7. extractionextracted with ethyl acetate
8. dry with materialThe extract was dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-ee3428d2d1754449943bfe5501798096

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06579882B2