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Dehydrohedione (DHH) 1a was obtained via a one pot, three step, domino procedure in 54% overall yield from 2a, by treatment with CuBr2, in MeOH at 65 °C. We demonstrated that the direct transformation of malonate derivative 2a into DHH 1a under CuX2 Kochi's conditions goes preferentially through the pathway involving intermediates 2b/2c and 7a, rather than 3a/3b or 8a/8b, essentially via α‐halogenation/dehydrohalogenation of the ketone moiety, both mediated by CuX2, while in‐situ decarbomethoxylation is promoted by the resulting CuX in refluxing MeOH.