The reaction of 2-alkynylanisoles/sulfides with SOCl2 and DMSO was conducted to conveniently furnish the biologically interesting 3-(methylthio)-benzo[b]furans/thiophenes via intramolecular cyclization.DMSO acts as a solvent as well as a sulfur source and can also be replaced with DMSO-d6,enabling the incorporation of the SCD3 moiety of DMSO-d6 to the 3-position of the heterocyclic frameworks.