An approach to synthesis of (Z)-2-chloro-1,3-diarylpropen-1-ones by Vilsmeier reagent (bis-(trichloromethyl) carbonate/DMF)

A series of (Z)-2-chloro-1,3-diarylpropen-l-ones were unexpectedly synthesized in moderate yields by treatment of easily available 2,3-epoxy-l, 3-diarylpropan-1-ones with Vilsmeier reagent, which was derived from bis(trichloromethyl) carbonate (BTC, triphosgene) and DMF. A possible mechanism was also proposed, where sequential ring-opening, halogenation and elimination reactions were involved.