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DOI: 10.1055/s-0029-1217223
Bromonitromethane: A Versatile Reagent in Organic Synthesis
Publikationsverlauf
Publikationsdatum:
02. Juni 2009 (online)
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Introduction
Bromonitromethane (BrCH2NO2) has received considerable attention as a one-carbon synthon for the synthesis of a variety of important organic intermediates. [¹] For examples, it was used in the synthesis of 2-nitrobenzofuran and 2-nitro-2,3-dihydrobenzofuran-3-ols, [²] nitrobenzothio-phenes, and nitrothiazoles, [³] polyfunctionalized nitrocyclopropanes. [4] It has also been utilized in the synthesis of 1-bromo-1-nitroalkan-2-ols [5] and aryl nitromethanes. In addition, it could be used as a bromine donor. [6]
Bromonitromethane is commercially available and can also be easily prepared according to the procedures reported by Fishwick et al. (Scheme [¹] ). [³] A typical procedure is as following: freshly distilled nitromethane was stirred at 0 ˚C and bromine was dropped in 5 seconds. The resulted bromonitromethane could be used without further purification. [¹a]
Scheme 1
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1a
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