An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine.
A method of producing a halogenated diene represented by formula (1): A1A2C═CA3-CA4═CA5A6[A1, A2, A5, and A6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A3 and A4 are each independently hydrogen, fluorine, or chlorine; at least one of A1 to A6 is hydrogen; at least one of A1 to A6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A7A8C═CA9X[A7 and A8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.