Synthesis of Ibuproxam

Ibuproxam의 합성

A convenient method for the synthesis of ibuproxam, which is a non steroidal antiinflammatory agent, is reported. Friedel-Crafts reaction of isobutylbenzene with ethyl $\alpha$-chloro-$\alpha$-(methylthio)acetate (3) gives ethyl $\alpha$-methylthio-(p-isobutylpheny) acetate (4). Ethyl 2-methylthio-2-(4-isobutylphenyl) propionate (5) is obtained from methylation of the compound (4) with NaH and Mel. lbuproxam (7) is easily synthesized by reductive desulfurization of the compound (5) with zinc dust-acetic acid or Raney nickel, followed by treatment of the resultant ethyl 2-(4-isobutyl-pheny) propionate (6) with H$_{2}$NOH-HCI.