The choice of solvent was found to have a profound effect on the performance of this cascade protocol, and despite a thorough screening we were unable to identify another solvent that gave better results than the initially selected DMA. Notably, conducting the reaction in dimethyl formamide (DMF) was found to result in a substantial reduction of the yield of 3 (41%), while the use of either acetonitrile (MeCN) or 1,2-dichloroethane (DCE) as solvents led to formation of amide but abolishment of the C-H chlorination process (Entry 8). In contrast, it was possible to obtain near quantitative yields of 3 in N-methylpyrrolidinone (NMP) if the reaction time was extended to 6 h (Entry 9). Encouragingly as shown by entry 10, this cascade protocol has the potential to be carried out in green solvents such as propylene carbonate and gamma-valerolactone (GVL), although further reaction optimizations are required to enable synthetically useful yields.