Triisopropyl borate → 4-(Trifluoromethyl)phenylboronic acid

Participants

Reaction Steps

To a solution of 1 mL (7.1 mmol) of 4-trifluoromethylphenyl bromide (JRD Fluoro Chemical LTD) in 20 mL of THF at −78° C. in a nitrogen atmosphere was added 7.1 mL (8.5 mmol) of nBuLi (1.6 M in THF). After stirring for 30 min, 2.5 mL (10.65 mmol) of triisopropyl borate (Aldrich) was slowly added and the reaction mixture was slowly warmed to rt. After 1 h at rt, the reaction mixture was concentrated and redissolved in 10 mL of a mixture of acetic acid and H2O (2:1). After stirring for 3 h, the reaction mixture was concentrated and redissolved in 100 mL of ethyl acetate. The solution was washed with sat'd NaHCO3 solution, and the organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated to give the title compound.

Provenance & Evidence