Boric acid (H3BO3), tripropyl ester → 3-Benzyloxy-phenylboronic acid

Temperature

-78 °C

20 g (76 mmol) of 3-Benzyloxybromobenzene was dissolved in 200 mL of anhydrous THF and cooled to -78° C. under a nitrogen atmosphere. To the stirring solution, 90 mL of 1.6 M n-BuLi (83.6 mmol) was slowly added. After several minutes, 33.6 mL (83.6 mmol) tripropylborate was added and the reaction was allowed to slowly warm to ambient temperature over the next four hours. The reaction was quenched with the addition of 400 mL of 1N HCl. The reaction mixture was extracted three times with EtOAc. The EtOAc solution was washed twice with brine, dried with Na2SO4, and evaporated to dryness. The final product was crystallized from EtOAc-hexane. This yielded 10 g of the title compound as a white solid.

1. waitAfter several minutes
2. temperatureto slowly warm to ambient temperature over the next four hours
3. customThe reaction was quenched with the addition of 400 mL of 1N HCl
4. extractionThe reaction mixture was extracted three times with EtOAc
5. washThe EtOAc solution was washed twice with brine
6. dry with materialdried with Na2SO4
7. customevaporated to dryness
8. customThe final product was crystallized from EtOAc-hexane

ORD record

ord-ed65f16852564c2d8ad36d1c1f88fc00

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05952350