Synthesis of cycloalkyldiarylphosphines

C - Chemistry – Metallurgy – 07 – F

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C07F 9/50 (2006.01)

Patent

CA 2249612

Partially sterically-hindered cycloalkyl chlorides are reacted with lithium diarylphosphides in inert liquid hydrocarbon reaction media to form cycloalkyldiarylphosphines. Aryl lithium is coproduced. The process makes it possible to avoid, or at least substantially eliminate, the interaction with or cleavage of cyclic ether reaction media such as tetrahydrofuran, previously the solvent of choice for conducting this type of reaction. Also during the conduct of the present process the chloro-substituted cycloalkane does not undergo any appreciable reaction with the coproduced aryl lithium as it is formed. Thus improvements both in yield and quality of the cycloalkyldiarylphosphine product are made possible. A comprehensive three- step process for converting triarylphosphine to cycloalkyldiarylphosphine is also described.

On fait réagir des chlorures de cycloalkyle à empêchement stérique partiel avec des diarylphosphides de lithium dans des milieux réactionnels d'hydrocarbure liquide, inerte afin d'obtenir des cycloalkyldiarylphosphines. On coproduit aussi l'aryl lithium. Ce procédé permet d'éviter ou au moins d'éliminer pratiquement l'interaction avec des milieux réactionnels éther cyclique ou le clivage de ces milieux, tels que le tétrahydrofuranne, solvant utilisé jusqu'à présent pour effectuer ce type de réaction. De plus, au cours de ce procédé, le cycloalcane chloro-substitué ne subit pas de réaction notoire avec l'aryl lithium coproduit, lors de sa formation. Il est par conséquent possible d'améliorer à la fois le rendement et la qualité du produit de cycloalkyldiarylphosphine. Un procédé complet en trois étapes servant à convertir le triarylphosphine en cycloalkyldiarylphosphine est également décrit.

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