Hydrochloric Acid → (2,6-Dimethoxyphenyl)boronic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 1,3-dimethoxybenzene (33.2 g, 240 mmol) in hexanes (20 mL) at −20° C. was treated sequentially with n-butyllithium (100 mL of a 2.4M solution in hexanes, 240 mmol) and N,N,N′,N′-tetramethylethylenediamine (1.81 mL, 12 mmol), stirred for 1.5 hours, cooled to −78° C., treated with triisopropylborate (60.9 mL, 264 mmol) in diethyl ether (60 mL) over 1.5 hours with additional diethyl ether (150 mL) added to maintain stirring, stirred at 23° C. for 2 hours, poured into ice (150 mL) and 3M HCl (150 mL), and extracted with ethyl acetate. The extract was dried (Na2SO4), filtered, and concentrated, during which a white solid precipitated. The solid was collected by filtration and washed with hexanes to provide the desired compound, which used without further purification. MS (DCI/NH3) m/z 200 (M+NH4)+.

Provenance & Evidence