2417-77-8

1468-95-7

2417-77-8

General procedure for the synthesis of 9-(bromomethyl)anthracene from 9-anthracenemethanol: To a stirred suspension of 9-anthracenemethanol (2.0 g, 9.6 mmol) in toluene (100 ml) at 0 °C was added dropwise phosphorus tribromide (PBr3, 1.2 mL, 12.51 mmol), and the reaction system was kept stirred at 0 °C for 1 hour. Subsequently, the reaction mixture was slowly warmed up to room temperature and stirring was continued for 1 h. It was observed that the mixture transformed into a yellow solution. Upon completion of the reaction, the reaction was quenched by the addition of aqueous potassium carbonate solution (10 mL). The toluene solvent was removed by rotary evaporator under reduced pressure. The residue was dissolved in ethyl acetate (EtOAc), and the organic phase was washed sequentially with saturated aqueous potassium carbonate solution, deionized water and saturated saline, and dried over anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure, and the resulting crude product was purified by fast column chromatography with the eluent of petroleum ether: ethyl acetate (2:1, v/v), which finally afforded the target compound 9-(bromomethyl)anthracene (47, 1.4 g, 54% yield) as a yellow solid. The product was characterized by 1H NMR (500 MHz, CDCl3): δ= 8.45 (1H, s, Ar-10H), 8.27 (2H, d, J=8.0 Hz, Ar-1,8H), 8.00 (2H, d, J=8.0 Hz, Ar-4,5H), 7.62 (2H, t, J=7.5 Hz, Ar-2,7H), 7.48 (2H, t, J=7.5Hz, Ar-3,6H), 5.50 (2H, s, CH2Br).