S(N)Ar reactions of 2-haloarylsulfoxides with alkoxides provide a novel synthesis of thiotomoxetine

Article abstract of DOI:10.1016/S0040-4039(99)00215-4

A five step synthesis of thiotomoxetine (2) is described. Installation of the aryl ether was accomplished using a highly efficient S(N)Ar fragment coupling between amino alcohol (4) and a 1-halo-2-methylsulfinylbenzene (X = F or Cl) followed by a selective reduction of the arylsulfoxide moiety.