Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran

Article abstract of DOI:10.1016/S0040-4020(96)00069-5

The synthetic potential of 3,4-dibromofuran has been assessed by its conversion into 3,4-disubstituted furans via mono-S-ipso-substitution. The ability of 3-methylthio and 3-phenylthio substituents for directing the metallation at position α-relative to the substituent has allowed the regiospecific alkylation. It provides a straightforward approach to several 3-monothiosubstituted furans which are receiving increasing interest as odour and flavour chemicals.