Abstract1,2‐Bis(trimethylsilyl)benzene is the key starting material for the synthesis of efficient benzyne precursors and certain luminescent π‐conjugated materials. We now report that it can be conveniently prepared in tetrahydrofuran from 1,2‐dibromobenzene, chlorotrimethylsilane, and either Rieke‐magnesium (MgR) or magnesium turnings in the presence of 1,2‐dibromoethane as an entrainer (Mge). The most important advantages of these new protocols over the currently best‐established procedure (1,2‐dichlorobenzene, chlorotrimethylsilane, magnesium turnings, hexamethylphosphoramide) lie in the milder reaction conditions (MgR: 0 °C, 2 h; Mge: room temperature, 30 min vs. 100 °C, 2 days) and in the fact that the cancerogenic solvent hexamethylphosphoramide is avoided. Moreover, the improved protocols are also applicable for the high‐yield synthesis of 1,2,4,5‐tetrakis(trimethylsilyl)benzene, 4‐fluoro‐1,2‐bis(trimethylsilyl)benzene, 4‐chloro‐1,2‐bis(trimethylsilyl)benzene, and 4,5‐dichloro‐1,2‐bis(trimethylsilyl)benzene.