Ethyl Acetate → (4-Methoxyphenyl)boronic acid

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence