Production method of tris(pentafluorophenyl)borane using pentafl

Details Production method of tris(pentafluorophenyl)borane using pentafl Production method of tris(pentafluorophenyl)borane using pentafl

1993-12-22

1996-04-23

Brust, Joseph Paul

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

Organic compounds

Boron containing

C07F 500

Patent

active

055105360

ABSTRACT:
A method of producing tris(pentafluorophenyl)borane or its ether complex, using pentafluorobenzene as the source of the pentafluorophenyl group. The process comprises reacting pentafluorobenzene with an organo metallic compound (II) of the formula R.sub.2-n MgX.sub.n, wherein n denotes a real number of 0 or 1, X denotes a halogen atom and R denotes a hydrocarbon group of 1 to 10 carbon atoms. The reaction is carried out in an ether solvent at a temperature not less than 25.degree. C. The resulting pentafluorophenylmagnesium compound has the formula (C.sub.6 F.sub.5).sub.2-n MgX.sub.n (III), wherein n denotes a real number of 0 or 1 and X denotes a halogen atom. The pentafluorophenylmagnesium compound of the formula (III) is next reacted with a borane compound of the formula BX.sub.3, wherein X denotes a halogen atom. The reaction is carried out at a temperature in the range of 0.degree. C. to 250.degree. C., preferably 60.degree. C. to 250.degree. C. in an ether solvent such as tetrahydrofurane or diethyl ether, or in a non-aqueous mixture of ether solvent and hydrocarbon solvent. The ether solvent forms a complex coordinated to tris(pentafluorophenyl)borane. The complexed solvent is eliminated by either direct or indirect eliminating processes. The product may then be reacted with 1:1 equivalents of pentafluorophenyllithium to prepare tetrakis (pentafluorophenyl)borate and subsequently mixed with a solution of N,N-dimethylanilinium to produce N,N-dimethylanilinium tetrakis(pentafluorophenyl)borate crystals. The final product is very pure with purities exceeding 98 wt. %. The anilinium product is usable as an auxiliary catalyst for cationic complex polymerization.

REFERENCES:
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Cohen et al., Adv. Fluorine Chemistry, 6, pp. 119-121 (1970).
Yang et al., JACS (1991), 113, 3623-3625.
CA 59: 8771 b, Chem. Abstract, Massey et al. (Proc. Chem. Soc., 1963 (Jul.), 212).
Chemical Abstracts, vol. 100, No. 17, Apr. 23, 1984, AN 139179s, Hiroshi Kobayashi, et al., "Synthesis of Trifluoromethylated Tetraphenylborates and the Solvent-Extraction Properties of Their Ion-Associates with Alkali-Metal Ions. Application of Tetraarylborates to Separation Analysis of Univalent Cations".
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