PURPOSE: To obtain an alkynyl halide compound useful as an intermediate for the industrial synthesis of a variety of pheromone substances in industrial high yield, by the reaction of a Grignard reagent with an ω-halo-1-bromoalkyne compound.
CONSTITUTION: An ω-halo-1-bromoalkyne compound expressed by formula I (n is 4, 5 or 6) in tetrahydrofuran is coupled with a solution of a Grignard reagent expressed by formula II (R is a monovalent hydrocarbon group; X is halogen) in tetrahydrofuran at a molar ratio between the Grignard reagent and the compound expressed by formula I of 1:1W1.5, preferably in the presence of a copper halide catalyst, e.g. cuprous bromide, at -5W10°C, to give the aimed compound expressed by formula III.
USE: A synthetic intermediate for cis,cis-7,11-hexadecadienylacetate, a sex pheromone substance of pink bollworms, etc.
YAMAMOTO AKIRA
TAGUCHI KENICHI
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