Hydrochloric Acid → (3-(Prop-1-yn-1-yl)phenyl)boronic acid

Participants

Reaction Conditions

Reaction Steps

n-Butyl lithium (2.5 M in hexanes, 3.7 mL, 9.4 mmol) was added dropwise to a solution of 1-bromo-3-(prop-1-ynyl)benzene (Intermediate 31, 1.66 g, 8.51 mmol) and triisopropyl borate (2.2 mL, 9.4 mmol) in tetrahydrofuran (5 mL) and toluene (15 mL) at −78° C. under an argon atmosphere. The reaction mixture was stirred for 30 min. and then allowed to reach r.t. and stirred for 1 h. The mixture was cooled to −78° C., and 3 M aq. hydrochloric acid was added and the mixture was stirred at r.t. for 15 min. The mixture was basified by addition of solid KOH. 2-methyl-tetrahydrofuran was added under stirring and the obtained solid was collected by filtration affording the title compound 1.0 g (75% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 2.01 (s, 3 H), 6.92-7.03 (m, 1 H), 7.09-7.20 (m, 1 H), 7.55-7.79 (m, 2 H).

Provenance & Evidence