PURPOSE: To obtain a conjugated diene compound useful as an organic intermediate, a raw material for high polymer industry, etc., by one stage, by reacting a metallic 1,3-butadienyl compound with an organic halide in the presence of a catalyst.
CONSTITUTION: A metallic butadienyl compound shown by formula I [M is MgX (X is Cl, Br or I) or Li] is reacted with an organic halide shown by the formula RX (R is 1W20C alkyl or aralkyl) in the presence of a copper catalyst (e.g. CuI or CuBr) in a solvent such as THF, diglyme, etc., in an inert gas flow to give a compound shown by formula II. When a Grignard reagent is used as the compound shown by the formula I, the Grignard reagent is added to an ether solution containing 10W30mol% based on 1mol organic halide of the copper catalyst and the organic halide and the reaction is carried out at -50W-20°C in addition and 0W25°C after the addition. When the lithium compound is used, 0.5W1.5mol copper catalyst is preferably used based on 1mol compound shown by the formula RX.
KASAI SANSEI
ISHII TOSHIYUKI
HITOMI TORAZO
TSUBOI TAKASHI
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