Bromonitromethane

UsesBromonitromethane has received considerable attention as a one-carbon synthon for the synthesis of a variety of important organic intermediates. Bromonitromethane is a key starting material for the preparation of the broad-spectrum antibiotic trovafloxacin, which contains the interesting 3-azabicyclo[ 3.1.0]hexane ring system. it was used in the synthesis of 2-nitrobenzofuran and 2-nitro-2,3-dihydrobenzofuran-3-ols, nitrobenzo­thio-phenes, and nitrothiazoles, polyfunctionalized nitrocyclopropanes. It has also been utilized in the synthesis of 1-bromo-1-nitroalkan-2-ols and aryl nitromethanes. In addition, it could be used as a bromine donor.

UsesBromonitromethane has been used:in production of various protected α-bromo nitroalkane donors (including Fmoc) for use in Umpolung amide synthesisin preparation of (Z)-1-bromo-1-nitroalkenes via sodium iodide-catalyzed Henry reactionin diastereo- and enantioselective cyclopropanation of β,γ-unsaturated a-ketoesters via domino Michael-addition/intramolecular-alkylation strategy

PreparationBromonitromethane is commercially available and can also be easily prepared according to the procedures reported by Fishwick et al. A typical procedure is as following: freshly distilled nitromethane was stirred at 0℃ and bromine was dropped in 5 seconds. The resulted bromonitromethane could be used without further purification.