A one-pot synthesis of ibuprofene involving three consecutive steps of superbase metalation

Article abstract of DOI:10.1016/S0040-4039(00)92708-4

A one-pot reaction sequence consisting of three consecutive metalation and electrophilic substitution stages leads to 2-(4-isobutylphenyl)propanoic acid with 52% over-all yield. A crucial step is the alkylation of deprotonated p-ethyltoluene with isopropyl bromide. In general terms, sec-alkyl halides and benzyl or allyl type alkalimetal reagents undergo coupling reactions with surprising ease.