I came across a chemistry problem posted on Discord. The objective is to propose a reagent that will enable the following reaction to occur:
One proposed answer for the mysterious Reagent D is sodium methanethiolate.The claim is made on the basis of the fact that patent US6777575B2 describes this exact sort of synthesis and calls for using MeSNa as a reagent in this situation. A counterargument is that the nitro group is stabilized through conjugation, and that methoxy or trifluoromethyl would be a better leaving group in this situation. Which claim is correct? In the reactant, can nitro act as a leaving group and allow for substitution with methanethiolate? Why or why not?