The simplicity of synthesis, such as in the preparation of pillar arenes, opens doors to the exploration of a receptor's chemistry. The short synthesis of pillar arenes often involves an initial step to make the functionalized building block followed by its macrocyclization. Typical pathways describe two steps taking 3 days on the 2-gram scale. Our intent in this present report is to offer the same invitation to the supramolecular community. As others begin to explore the chemistry of cyanostar, and requests are fielded for more guidance on the original procedures, a description of the optimized procedures was warranted. Herein, we report a pair of updated synthesis pathways for cyanostar that are tailored towards either large >25-g scales or fast <5-g reaction times (2 days). Both scales are described herein, a comparison of the hazards, reaction times and overall yield for both methods are outlined, and additional tips and tricks are provided in the Supplementary Information. was considered complete, and it was removed from the heat to avoid formation of undesired dibrominated product. The reaction mixture was concentrated in vacuo to remove most of the toluene. Saturated NaHCO3 solution (200 mL) was added to neutralize the acid and the mixture washed with brine. The monobrominated product was extracted with CH2Cl2 (150 mL × 3), the organic phases dried over MgSO4 and concentrated in vacuo to yield 4 as a yellow oil (24 g, 95%).