2-[4-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used in the synthesis of metalloproteinase-13 inhibitors in the treatment of osteoarthritis.
Pinacol p-tolueneborate (10.91g, 50.0mmol), bromosuccinimide (NBS, 9.91g, 55.0mmol), and azobisisobutyronitrile (AIBN, 0.44g, 2.0mmol) were dissolved in dry of carbon tetrachloride (CCl4, 200 mL), stirred at reflux for 14 hours. The mixture was filtered, the solvent was evaporated, and the mixture was dissolved in ethyl acetate (200 mL). Wash once with distilled water (100 mL) and saturated sodium chloride aqueous solution (100 mL), dry with anhydrous sodium sulfate, and rotary evaporate. Finally, use petroleum ether as the eluent for column chromatography separation to obtain 4-(Bromomethyl)benzeneboronic acid pinacol ester
(11.30g, yield 76.1%).
