Abstract
The accessibility of bromonitromethane has declined in recent years, limiting its viability as a reagent for chemical synthesis. The reinvestigation and optimization of a variety of preparations, and the development of safe operating principles, are described. The reproducible protocol described here leverages the effectiveness of hydroxide for nitromethane bromination while respecting its incompatibility with the product it forms. This careful balance was achieved at scales up to 56 g, resulting in a reproducible procedure that provides straightforward, sustainable, and affordable access to this critical reagent.
Madelaine P. Thorpe, Abigail N. Smith, Michael S. Crocker, and Jeffrey N. Johnston, The Journal of Organic Chemistry, 2022, 87 (8), 5451-5455. DOI: 10.1021/acs.joc.2c00405
https://doi.org/10.1021/acs.joc.2c00405