15442-91-8

95-93-2

15442-91-8

General procedure for the synthesis of tetrabromotoluene from 1,2,4,5-tetramethylbenzene: 1,2,4,5-tetrakis(bromomethyl)benzene (2.8 g, 20 mmol) was prepared by reacting 1,2,4,5-tetramethylbenzene (2.8 g, 20 mmol) with N-bromosuccinimide (NBS, 14.4 g, 80 mmol) and benzoyl peroxide in 50 mL of tetrachloromethane (1c, 1 g, 5.9 mmol). The reaction mixture was heated at 77 °C for 50 min. After completion of the reaction, the precipitate was collected by filtration under reduced pressure and washed with hot tetrachloromethane. The filtrate was concentrated to a small volume and cooled to 4 °C. The crude product was filtered and purified by recrystallization from methanol. The reaction time was less than 1 hour to give a white solid product in 15% yield with a melting point of 159-160°C. The structure of the product was determined by 1H-NMR (CDCl3, δ: 7.37 ppm, 2H, a; 4.60 ppm, 8H, b), 13C-NMR (CDCl3, δ: 137.6 ppm, a; 133.6 ppm, h; 28.7 ppm, b), and FT-IR (KBr, νmax: 3026, 2980, 2933. 1504, 1456, 1210, 911, 797, 678, 598 cm-1) were characterized.