Cyclic carbonates are a highly versatile monomers class with a broad set of applications ranging from antimicrobial and anticancer polycarbonate materials to high-performance polyurethanes. Automated synthesis via continuous-flow platforms offers a means to greatly reduce experimental overhead required to access new polycarbonate material systems. However, the synthesis of cyclic carbonate monomers is often highly tedious, requiring multiple steps, toxic or expensive reagents, and typically affords low to modest yields. This places a large labor and cost barrier to fully utilize advances in experimental automation to accelerate polycarbonate materials discovery. Here, we demonstrate a simplified approach to preparing cyclic carbonate monomers that obviates the need for highly toxic reagents and long synthetic sequences. The implications of this work in the context of utilizing automated continuous-flow platforms for polymer synthesis will also be presented.