Process for preparing fluoroaryl magnesium derivative and proces

Details Process for preparing fluoroaryl magnesium derivative and proces Process for preparing fluoroaryl magnesium derivative and proces

1997-10-16

2000-05-02

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Boron containing

568 1, 260665G, C07F 502

Patent

active

060574801

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a process for preparing a fluoroaryl magnesium derivative which is suitably used, for example, as a reactant (organic synthetic reagent) for introducing a fluoroaryl group into various kinds of organic compounds. The present invention also relates to a process for preparing a (fluoroaryl)borane compound, such as tris(fluoroaryl)borane and bis(fluoroaryl)boryl halide, serving, for example, as an excellent cocatalyst for a metallocene catalyst (polymeric catalyst) used in a cation complex polymerization reaction.


BACKGROUND ART

A fluoroaryl magnesium derivative, which is a Grignard reagent, is well known, for example, as an excellent reactant (organic synthetic reagent) for introducing a fluoroaryl group into various kinds of organic compounds. Also, in recent years, the fluoroaryl magnesium derivative has been receiving considerable attention as a synthetic material of a tris(fluoroaryl)borane compound serving as an excellent cocatalyst for a metallocene catalyst (polymeric catalyst).
A process for preparing a fluoroaryl magnesium derivative is disclosed, for example, in J. Org. Chem., 29, 2385 (1964). More specifically, an alkyl magnesium derivative, such as ethyl magnesium bromide (EtMgBr), is dropwise to a solution prepared by dissolving pentafluorobenzene into an ether solvent, such as tetrahydrofuran (THF). Consequently, a pentafluorophenyl magnesium derivative is obtained as the fluoroaryl magnesium derivative. Japanese Laid-open Patent Application No. 247976/1994 (Tokukaihei 6-247976) discloses another process. In this process, the pentafluorophenyl magnesium derivative is obtained by adding a solution prepared by dissolving pentafluorobenzene into an ether solvent to another solution prepared by mixing an alkyl magnesium derivative with the ether solvent.
In these processes, the pentafluorophenyl magnesium derivative is obtained through an exchange reaction, in which an alkyl group in the alkyl magnesium derivative is replaced with a pentafluorophenyl group.
However, in these processes, the alkyl magnesium derivative is produced before the above exchange reaction is carried out to obtain the pentafluorophenyl magnesium derivative. In other words, since the alkyl magnesium derivative is prepared separately before obtaining the pentafluorophenyl magnesium derivative, the reaction takes place in two steps.
To solve the above problem, the present invention has a first object to provide a process for producing the fluoroaryl magnesium derivative efficiently at a low cost in a simple manner virtually in a single step reaction.
A (fluoroaryl)borane compound, particularly, tris(pentafluorophenyl)borane, is known, for example, as an excellent cocatalyst for promoting the activity of a metallocene catalyst (polymeric catalyst) used in a cation complex polymerization reaction, and recently, the metallocene catalyst has been receiving considerable attention as a polyolefin polymerization catalyst.
An example process of obtaining the above-mentioned tris(pentafluorophenyl)borane is disclosed in Proc. Chem. Soc., 1963 (July), 212. More specifically, pentafluorobenzene lithium produced by reacting bromopentafluorobenzene and butyl lithium is reacted with boron trichloride, and as a consequence, tris(pentafluorophenyl)borane is obtained. However, in this process, the reaction system must be cooled to 78.degree. C., which makes this process almost inapplicable for industrial use.
To solve the above problem, a process using the Grignard reaction is disclosed in Z. Naturforsch., 20b, 5 (1965) as another example process of obtaining the tris(pentafluorophenyl)borane. According to this process, for example, pentafluorophenyl magnesium bromide and boron trifluoride diethyl etherate are reacted with each other in a chain ether solvent. Thus, it is not necessary to cool the reaction system to -78.degree. C., which makes this process advantageous over the above-mentioned reaction. Further, Japanese Laid-open Patent Application No. 199871/1994 (Tokukaihei 6-199871) disclos

REFERENCES:
patent: 5399780 (1995-03-01), Ikeda
patent: 5510536 (1996-04-01), Ikeda
patent: 5693261 (1997-12-01), Ikeda
CA:86:5504, abs of"Use of diisopropyl ether as a medium form butylmagnesium chloride production", Ratanova, Zh Prikl Khim, 49 (*), pp. 1864-1868, 1976.
CA:67:43845 abs of"Preparation of ethyl magnesium chloride in hydrocarbon solvent", Smai, Chim Ind (Milan),49(2), pp. 142-146, 1967.

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