1265682-43-6Relevant articles and documents
Improved synthesis of 1,2-bis(trimethylsilyl)benzenes using Rieke-magnesium or the entrainment method
Lorbach, Andreas,Reus, Christian,Bolte, Michael,Lerner, Hans-Wolfram,Wagner, Matthias
supporting information; experimental part, p. 3443 - 3449 (2011/02/24)
1,2-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. Copyright
