The multicomponent assembly of a nitrile-based directing group in a set of arylacetic acids under solvent-free mechanochemical conditions using the Passerini 3-CR and the subsequent Pd(II)-mediated meta-C(sp2)-H bond olefination process has been achieved. The protocol demonstrated that removing the DG under mild conditions from the activated Passerini adducts affords a novel N-(tert-butyl)-2-(2-cyanophenyl)-2-hydroxyacetamide, which can be re-utilized in the future as DG in other distal activation processes.