Synthesis
General procedure for the synthesis of 1,2-bis(dimethylsilyl)benzene from dimethylmonochlorosilane and 1,2-dibromobenzene: a condenser was assembled in a dry 50 mL two-necked flask, and stirring bars, magnesium powder (99.9%, 24 mmol), lithium chloride (24 mmol), N,N'-dimethylimidazolidinone (DMI, 20 mL) and chlorodimethylsilane ( 48 mmol). After stirring the reaction mixture for 15 minutes at room temperature, 1,2-dibromobenzene (3 mmol) was added and stirring was continued for 4 hours. After completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution. The sodium bicarbonate and the resulting precipitate were removed by filtration. The filtrate was extracted with hexane (3 x 20 mL), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated by rotary evaporation. The crude product was purified by silica gel column chromatography, and the eluent was pure hexane or hexane/dichloromethane mixed solvent.
References
[1] Synthesis (Germany), 2017, vol. 49, # 11, p. 2495 - 2500
[2] Tetrahedron Letters, 2000, vol. 41, # 34, p. 6611 - 6614
[3] Tetrahedron, 1993, vol. 49, # 43, p. 9855 - 9866
[4] Journal of Organometallic Chemistry, 2018, vol. 854, p. 76 - 86
[5] Tetrahedron, 1991, vol. 47, # 47, p. 9807 - 9822
