Example 1: Preparation of compound C-12
Preparation of Compound 2 [(4-phenylnaphthalen-1-yl)boronic acid]
[1081] 1-bromo-4-phenylnaphthalene (Compound 1) (50 g, 176 mmol) was dissolved in anhydrous tetrahydrofuran (THF) (1 L) in a flask. The mixture was stirred at -78°C and n-butyllithium (n-BuLi) (2.5 M in hexane, 132 mL) was added slowly and dropwise. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was cooled to -78°C and triisopropyl borate (61 mL, 264 mmol) was added slowly and dropwise. The reaction mixture was then stirred at room temperature for 3 hours. After completion of the reaction, extraction was carried out with ethyl acetate. The organic layer obtained from the extraction was dried with magnesium sulfate (MgSO) and solidified by hexane to give compound 2 (30 g, 68% yield).
