The synthesis of 9-phenylanthracene involved mixing phenylboronic acid (2.13 g, 17.49 mmol), 9-bromoanthracene (3 g, 11.66 mmol), Pd(PPh3)4 (140 mg, 0.12 mmol), K2CO3 (16 mL, 2 M), and ethanol (8 mL) in a 100 mL flask with anhydrous toluene (32 mL). The mixture was refluxed for 48 h under nitrogen. After cooled to room temperature, the reaction mixture was quenched with dilute hydrochloric acid solution and extracted with CH2Cl2. The organic extracts were dried over anhydrous MgSO4 and concentrated by rotary evaporation. The crude product was further purified by silica gel column chromatography (CH2Cl2/petroleum ether (1:4,v/v)) to get a white powder (2.43 g, 81.9 %). 1H NMR (500 MHz, CDCl3) δ 8.53 (s, 1H), 8.08 (d, J = 8.5 Hz, 2H), 7.70 – 7.67 (m, 2H), 7.63 – 7.54 (m, 3H), 7.50 – 7.45 (m, 4H), 7.37 (ddd, J = 8.7, 6.5, 1.2 Hz, 2H). EI-MS (m/z): Calculated for C20H14: 254.33. Found [M+]: 253.02.
Synthesis of 9-phenylanthracene
