Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States.
J Org Chem. 2022 Apr 15;87(8):5451-5455. doi: 10.1021/acs.joc.2c00405. Epub 2022 Apr 1.
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.
近年来,溴硝基甲烷的可获得性下降,限制了其作为化学合成试剂的可行性。本文对各种制备方法进行了重新研究和优化,并制定了安全操作原则。这里描述的可重复方案利用了氢氧化物对硝基甲烷进行溴化的有效性,同时尊重了它与产物的不相容性。在高达 56 克的规模下实现了这种精细的平衡,从而得到了一种可重复的方法,为获得这种关键试剂提供了简单、可持续和经济实惠的途径。