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Under an argon gas atmosphere, a mixture of 212 g (748 mmol) of <strong>[667940-23-0]2(3-bromophenyl)naphthalene</strong> and 3 L of dehydrated TI-IF was cooled down to minus 10 degree C., and 600 ml (948 mmol) of hexane solution of 1.6M n-butyllithium was dropped into the mixture while the mixture was being stirred. Then, the mixture was stirred at 0 degree C. for 2 hours. The reaction solution was again cooled down to minus 78 degrees C., and 450 g (2.39 mol) of triisopropylborate was dropped into the solution. Then, the solution was stirred at room temperature for 17 hours. The reaction mixture was added with aqueous solution of hydrochloric acid and stirred at room temperature for 1 hour. The reaction mixture was added with 3 L of toluene, and aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 126 g of 3-(2-naphthyl)phenylboronic acid was obtained at an yield of 67%.
50%
13-B. Preparation of compound 13b; [200] Under N atmosphere, to a compound 13a (4 g, 14.1 mmol) prepared in 13-A, dehydrated ether (80 mL) and dehydrated toluene (80 mL) were added, and cooled to - 640C in ice bath. A 2.5 M butyl lithium/hexane solution (6 mL) was added drop wise thereto for 30 minutes, and subjected to reaction at -640C for 2 hours. Boronic acid triisoester (9 mL) was added dropwise thereto for 15 minutes, and then stirred at room <n="75"/>temperature for 12 hours. After ice cooling, 2 N hydrochloric acid (35 rnL) was added at 1O0C or lower and toluene (10 mL) was added. The mixture was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was re- crystallized from EtOH to prepare a compound 13b (1.75 g, 50%).
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; toluene;
(2) Synthesis of Compound 2-2 Under an argon gas atmosphere, a mixture of 212 g (748 mmol) of 2(3-bromophenyl) naphthalene and 3 L of dehydrated THF was cooled down to -10 degrees C., and added with 600 ml (948 mmol) of hexane solution of 1.6M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at 0 degree C. The reaction solution was further cooled down to -78 degrees C., and added with 450 g (2.39 mol) of triisopropyl borate in drops. Subsequently, the reaction mixture was stirred for 17 hours at room temperature. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature. The reaction mixture was further added with 3 L of toluene, so that aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 126 g of 3-(2-naphthyl) phenylboronic acid was obtained at an yield of 67%.
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