Ethyl Acetate → (4-Methoxyphenyl)boronic acid

Temperature

-78 °C

To a solution of 4-iodoanisole (26) (5 g) in THF (45 ml), n-BuLi in n-hexane solution (1.6 M) (16.02 ml) was added at -78° C. under the inert atmosphere. The reaction mixture was stirred at -78° C. for 1 hr, then a tri (i-propyl) borate (5.9 ml) was added. The reaction mixture was stiffed at room temperature for 2 hrs. The reaction mixture was cooled to room temperature and poured into satd. NH4Cl aq. The resulting solution was added with ethyl acetate and was stirred at room temperature for 1.5 hrs. The reaction mixture was extracted with ethyl acetate and then the organic layer was washed with satd. NH4Cl aq, water and brine. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The concentrate was crystallized with n-hexane-ether (4:1). The resulting precipitate was collected by filtration. 4-methoxyphenylboronic acid (27) was obtained as a white crystal (1.98 g).

1. waitThe reaction mixture was stiffed at room temperature for 2 hrs
2. temperatureThe reaction mixture was cooled to room temperature
3. additionpoured into satd
4. stirringwas stirred at room temperature for 1.5 hrs
5. extractionThe reaction mixture was extracted with ethyl acetate
6. washthe organic layer was washed with satd
7. dry with materialThe organic layer was dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe concentrate was crystallized with n-hexane-ether (4:1)
11. filtrationThe resulting precipitate was collected by filtration

ORD record

ord-c5e8532042284ef0838c28f403358dc5

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06124460