A microscale organic laboratory experiment for the synthesis of 4'-phenyl-acetanilide via a Suzuki cross-coupling reaction using student-generated para-bromoacetanilide as substrate is presented. The methodology employs recent advances for the “greening” of the Suzuki reaction by using water as solvent, TBAB (tetra-n-butylammonium bromide) for solvation assistance, and a small amount (1 mol %) of palladium acetate as catalyst. The solid product is easily purified by microcolumn chromatography and characterized by melting point, 1H, and 13C NMR spectroscopy. Pedagogical advantages of this multi-step sequence include: student exposure to contemporary trends in organic synthesis employing transition metal-mediated catalysis, interpretation of intermediate-level NMR spectra, and contextual applications of thin layer and gravity column chromatographic techniques. This experiment also reinforces an emphasis on Green Chemistry and microscale practices in modern organic synthesis.
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Pantess et al. (2009) studied this question.
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