Synthesis of bromodifluoromethyl phenyl sulfide,sulfoxide and sulfone [1]

Sodium thiophenoxide reacts with dibromodifluoromethane to give bromodifluoromethyl phenyl sulfide. Peracid oxidation of the sulfide gives the corresponding sulfoxide and sulfone. The formation of the sulfide is suggested to proceed $\text{via}$ attack of thiophenoxide on halogen to produce difluorocarbene. Capture of carbene by thiophenoxide followed by a second positive halogen abstraction reaction yields the sulfide, PhSCF₂Br. The use of excess sodium thiophenoxide yields difluorobis(thiophenyl)methane, (PhS)₂CF₂, $\text{via}$ a similar mechanistic scheme.