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A Closer Look at the Bromine–Lithium Exchange with tert-Butyllithium in an Aryl Sulfonamide Synthesis
- Waldmann, Christopher, Schober, Otmar, Haufe, Günter, Kopka, Klaus
- Organic letters 2013 v.15 no.12 pp. 2954-2957
- bromides, chemical reactions, chemical structure, sulfonamides, synthesis
- A practical protocol for the one-pot synthesis of various aryl sulfonamides, notably of pyridine-core-substituted 7-azaindolyl sulfonamides, is described. A key step is the well-known bromine–lithium exchange reaction of an aryl bromide with tert-butyllithium (t-BuLi). Differing from the common practice to use 2 or more equiv of organolithium, the exact amount of t-BuLi needed for a sufficient exchange reaction is determined for each aryl bromide in a GC–MS-assisted experiment.