Synthesis
General procedure for the synthesis of 1-(4-fluorophenyl)-2-pyrrolidinone from 2-pyrrolidinone and p-fluoroiodobenzene: N-nucleophilic reagent (2.21 mmol), Cu2O (Sigma-Aldrich, 99.99% purity, 0.147-0.294 mmol), K3PO4 (2.94 mmol), aryl halide (1.47 mmol), phase transfer catalyst (0.147-0.294 mmol) and water (0.40 mL) were sequentially added to the reaction vial and sealed by installing a screw cap. The reaction mixture was stirred in a closed system at 130 °C for 24 h under air atmosphere. Upon completion of the reaction, the non-homogeneous mixture was cooled to room temperature and diluted with dichloromethane. The resulting solution was filtered directly through diatomaceous earth. The organic extracts were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography to afford the N-arylated product 1-(4-fluorophenyl)-2-pyrrolidinone. The structure and purity of the product were confirmed by 1H NMR and 13C NMR spectral analysis.
References
[1] Tetrahedron Letters, 2011, vol. 52, # 11, p. 1169 - 1172
[2] Synlett, 2015, vol. 26, # 12, p. 1697 - 1701
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2178 - 2182
