1. Preparation of Compound 2a: 1-Bromo-3-iodobenzene (10 g, 35.35 mmol) and 2-naphthaleneboronic acid (5.47 g, 31.82 mmol) were dissolved in anhydrous tetrahydrofuran (THF, 100 mL) under dry conditions. Subsequently, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.2 g, 1.06 mmol) and 2M aqueous potassium carbonate (K2CO3) (50 mL) were added. The reaction mixture was heated to reflux for 24 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate and dried with anhydrous magnesium sulfate (MgSO4). After filtration to remove the desiccant, the organic layer was concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography followed by recrystallization in a solvent mixture of tetrahydrofuran (THF) and ethanol (EtOH) to afford the white solid compound 2a (8.5 g, 85% yield). Mass spectrometry analysis showed [M + H]+ peak located at 283 m/z.
