2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile

Synthesis

A mixture of dichloro[1 ,1 ,'-bis(diphenylphosphino)ferrocene] palladium (II) dichloromethane adduct (2.12 g, 2.55 mmol), potassium acetate (7.66 g, 76.5 mmol), and bis(pinacolato) diboron (7.12 g, 28.1 mmol) was flushed with nitrogen. 1 ,2- dimethoxyethane (130 ml ) and 4-bromo-2-methylbenzonitrile (5.00 g, 25.5 mmol) were added. The reaction was stirred at 80°C for 5 h. The reaction was cooled to room temperature and filtered through celite. The filtrate was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. Silica gel was added and the mixture was concentrated. Finally, the crude material was purified by silica column chromatography eluting with a gradient of 0%- 45% ethyl acetate / heptane to give 2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (5.07 g, 82%) as a white solid.