Halogen/lithium exchange in hydrocarbon media; basic and continuous reactor studies

The halogen/lithium (X/Li) exchange's usefulness is challenged by the extreme conditions employed during the conversion of a bromo or an iodo substituent to an organolithium intermediate. Our preliminary disclosure reveals that simple X/Li exchanges can be accomplished at ambient temperature and in doped hydrocarbon media using n-BuLi. Use of a continuous reactor featuring brief reaction times (⩽1 s) and large product throughputs further facilitates the production of a product resulting from a sequential X/Li exchange and nucleophilic addition.