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Step 1 : Synthesis of 5-cyano-2-methylphenylboronic acid First, 9.5 g (50 mmol) of <strong>[42872-74-2]3-bromo-4-methylbenzonitrile</strong> was put into a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. Then, 250 mL of tetrahydrofuran (THF) was added, and the mixture was stirred at -78 C for 30 minutes. Into this mixed solution, 34 mL (55 mmol) of a 1.63M hexane solution of -butyllithium (-BuLi) was dropped, followed by stirring at -78 C for 1.5 hours. After that, 7.3 mL (65 mmol) of trimethyl borate was added to the mixture and this solution was stirred for 20 hours while the temperature was raised to room temperature. To this solution was added 100 mL of 1M hydrochloric acid and stirring was performed for 30 minutes. The obtained mixture was separated to an aqueous layer and an organic layer, and the aqueous layer was subjected to extraction with ethyl acetate. The organic layer and a solution of the extract were combined, and washed with saturated saline. Anhydrous magnesium sulfate was added to the obtained solution for drying. The obtained mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. This solid was washed with toluene and hexane, so that 4.3 g of a white solid was obtained in a yield of 53 %. The obtained white solid was identified as 5-cyano-2-methylphenylboronic acid by nuclear magnetic resonance ( MR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-10) below.
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