Next, we envisioned a synthetic route towards a bifunctional catalyst consisting of the chiral phosphoric acid backbone and 2CzPN as the attached photocatalyst, motivated by positive reports on the performance of 2CzPN as an energy transfer catalyst. To achieve this, a slightly different approach was used to access a brominated derivative of 2CzPN (9) as depicted in Scheme 5. Even though the synthesis of 9 was described in the literature, our attempts at replicating the reported procedure for the synthesis of intermediate 8 were hindered by both incomplete reactivity and over addition of the carbazole, which presented challenging issues related to purification. Attempts to optimize the reaction conditions to give 8 in a quantitative yield were unsuccessful and instead a mixture of 8, starting material and double substituted material (2CzPN) was obtained in all cases. Purification of this mixture by column chromatography was not trivial. By observing that the desired molecule 8 displayed lower solubilities in chloroform and DCM than the symmetric unwanted products (difluoro starting material and 2CzPN), we were able to develop a new purification process to obtain clean 8 through multiple rounds of washes with chloroform/DCM. Scheme 5: Synthesis of brominated 2CzPN-derivative 9 and monosubstituted 8.