Triisopropyl borate → [2-(2-Methoxyethoxy)phenyl]boronic acid

Temperature

-78 °C

To a solution of the compound of step 1 (2.20 g, 7.91 mmol) in toluene (20 ml) and THF (4 ml) was added triisopropyl borate (2.19 ml, 9.49 mmol), and the mixture was cooled to −78° C. n-Butyllithium (3.79 ml, 9.49 mmol, 2.5 M in hexane) was added dropwise and the reaction mixture was stirred at −78° C. for 1.5 h. The cooling bath was removed and the reaction mixture was allowed to warm to −20° C. Then 2 N hydrochloric acid (7 ml) was added. When the mixture had reached room temperature, water and EA were added. The organic layer was separated, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (EA/HEP 1:4). 766 mg of the title compound were obtained.

1. additionwas added dropwise
2. customThe cooling bath was removed
3. temperatureto warm to −20° C
4. additionThen 2 N hydrochloric acid (7 ml) was added
5. customhad reached room temperature
6. additionwater and EA were added
7. customThe organic layer was separated
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. customevaporated in vacuo
11. customThe residue was purified by silica gel chromatography (EA/HEP 1:4)

ORD record

ord-30f0fccb2b6643a9807125402751c9d4

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211885B2