A scalable process for a pilot plant synthesis of methyl 2-bromo-6-chlorobenzoate (1) is described. The strategy employed for the synthesis hinged on the esterification of the sterically encumbered parent acid produced through an o-lithiation/ carboxylation approach. Vigilant temperature control was paramount for the success of this synthetic pathway. Initiation of an exothermic benzyne decomposition pathway during the o-lithiation step occurred at -70 °C. In the pilot plant, cooling via the jacket service was suitable to provide batch temperatures of -75 °C. However, control of reaction heat required liquid nitrogen injection into the process vessel simultaneously with the exothermic reagent charges. Esterification of the carboxylic acid was accomplished with potassium carbonate/methyl iodide, and subsequent crystallization resulted in 79% overall yield of the title compound from inexpensive starting materials.