The general procedure for the synthesis of 9,10-bis(2-naphthalenyl)anthracene-2-boronic acid from 2-bromo-9,10-bis(2-naphthalenyl)anthracene and trimethyl borate was as follows: 2-bromo-9,10-bis(2-naphthalenyl)anthracene (10.00 g, 19.63 mmol, 1.0 eq.) was dissolved in THF (140 mL) according to the methodology described in EP13, and the solution was cooled to -78°C. At this temperature, n-butyllithium (2.5 M hexane solution, 10.2 mL, 25.52 mmol, 1.3 eq.) was slowly added dropwise, followed by stirring the reaction mixture for 2 hours. Next, trimethyl borate (6.12 g, 58.89 mmol, 3.0 eq.) was added at -78 °C and the reaction mixture was gradually warmed to room temperature. After the reaction was stirred continuously for 17 h, the reaction was quenched with hydrochloric acid solution, the resulting yellow precipitate was collected by filtration and washed with distilled water (2 x 30 mL). Finally, the resulting solid was dried under vacuum and used for subsequent reactions without further purification. Yield: 9.8 g (100%).
