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Synthetic method for tetra(pentafluorophenyl)borate

A technology of pentafluorophenyl and synthetic method, applied in the field of tetraborate synthesis, can solve problems such as unfavorable industrialized production, harsh reaction conditions, harsh synthesis conditions, etc., and achieves strong technological and operational practicability, low cost, and steps simple effect

Inactive Publication Date: 2015-12-16
SHANGHAI SINOFLUORO SCI
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  • Abstract
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  • Claims
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Problems solved by technology

The shortcoming that this synthetic method exists is very obvious, and that must use three (pentafluorophenyl) borane intermediates
Another important synthetic method is the one-step reaction of haloborane and pentafluorophenyllithium, but pentafluorophenyllithium will decompose above -30°C, especially haloborane is not easy to operate, so the synthesis conditions are extremely harsh (US2003083526A1; WO98 / 22470A1; Chem. Eur. J. 2007, 13: 7933-7947; Journal of Organometallic Chemistry, 2000, 597: 92-104)
[0004] As mentioned above, in the prior art, the synthetic method of synthesizing tetrakis (pentafluorophenyl) borate has harsh reaction conditions, long reaction route, and high cost, which is unfavorable for industrialized production

Method used

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  • Synthetic method for tetra(pentafluorophenyl)borate
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  • Synthetic method for tetra(pentafluorophenyl)borate

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[0044] Method 1: Specifically, when M + When it is an organic carbocation or an organic ammonium ion, a synthetic method of tetrakis (pentafluorophenyl) borate is provided, comprising the following steps: using pentafluorobromobenzene as a starting material, first treating with isopropylmagnesium chloride , and then react with trimethyl borate to obtain the precursor tetrakis (pentafluorophenyl) borate magnesium salt (I), and then carry out cation exchange to obtain the product compound (II); the reaction scheme of the method is:

[0045]

[0046] In a preferred embodiment, in the synthesis method, the M + It is triphenylcarbenium ion or N,N-dimethylanilinium ion.

[0047] In a further preferred embodiment, the synthesis method comprises the following steps:

[0048] (1) Prepare the required Grignard reagent: under nitrogen protection, add 2-methyltetrahydrofuran (moisture<100ppm), magnesium chips, at least 1 drop of 1,2- Dibromoethane, stir, first drop 1 / 10-1 / 5 of 2-chl...

Embodiment 1

[0073] Synthesis of Triphenylcarbenium Tetrakis(pentafluorophenyl)borate

[0074] (1) Under the protection of nitrogen, add 400ml of 2-methyltetrahydrofuran (moisture <100ppm), 39.28g of magnesium chips, and 1 drop of 1,2-dibromoethane into a four-necked flask equipped with a reflux condenser (through low temperature liquid). , stir, add 125.6g 2-chloropropane and 304ml 2-methyltetrahydrofuran to the constant pressure dropping funnel, first drop in 1 / 10 of 2-chloropropane in 2-methyltetrahydrofuran solution, heat to 40°C, condense and reflux, After the reaction of the dropped 2-chloropropane is completed, add the remaining 2-chloropropane dropwise, react at 40°C until the 2-chloropropane reacts completely, and make a 2-methyltetrahydrofuran solution of isopropylmagnesium chloride, and measure its concentration by titration. The concentration is about 1.89mol / L;

[0075] (2) Under the protection of nitrogen, add 160g of pentafluorobromobenzene and 1000ml of toluene to the four...

Embodiment 2

[0079] Synthesis of N,N-Dimethylanilinium Tetrakis(pentafluorophenyl)borate

[0080] (1) Under the protection of nitrogen, add 400ml of 2-methyltetrahydrofuran (moisture <100ppm), 39.28g of magnesium chips, 3 drops of 1,2-dibromoethane , stir, add 125.6g 2-chloropropane and 304ml 2-methyltetrahydrofuran to the constant pressure dropping funnel, first drop 1 / 5 of 2-chloropropane in 2-methyltetrahydrofuran solution, heat to 40°C, condense and reflux, After the reaction of the 2-chloropropane that has been dropped, add the remaining 2-chloropropane dropwise, react at 40°C until the 2-chloropropane reacts completely, and make a 2-methyltetrahydrofuran solution of isopropylmagnesium chloride, and measure its concentration by titration About 1.89mol / L;

[0081] (2) Under the protection of nitrogen, add 160g of pentafluorobromobenzene and 1000ml of toluene into the four-necked flask, stir and cool down to 0°C, add 321ml of isopropylmagnesium chloride in 2-methyltetrahydrofuran solut...

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Abstract

The invention provides a synthetic method for tetra(pentafluorophenyl)borate. The synthetic method comprises the following steps: with pentafluorobromobenzene as a starting raw material, treating pentafluorobromobenzene with organic lithium or a Grignard reagent so as to obtain an intermediate A; reacting the intermediate A with trimethyl borate; and carrying out post-treatment so as to obtain the target product tetra(pentafluorophenyl)borate with a structural formula described in the specification. M+ in the product of the method is any one selected from the group consisting of organic carbocation, organic ammonium ion and alkali metal ion. Compared with the prior art, the invention has the following advantages: usage of tri(pentafluorophenyl)borane sensitive to water and oxygen is avoided; product yield is high; and the method has good process and operation practicality, simple steps and low requirements on equipment and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing borate, in particular to a method for synthesizing tetrakis(pentafluorophenyl) borate. Background technique [0002] Tetrakis(pentafluorophenyl)borate is an important fine chemical used in catalysts such as metallocene polyolefin catalysts, hydrogen storage materials, etc., especially as an important core co-catalyst in metallocene catalyst systems, and has very important uses , by ionizing metallocene compounds, exhibiting a singular performance of catalyzing olefin polymerization. [0003] Tetrakis(pentafluorophenyl) borate is easier to handle than tris(pentafluorophenyl)borane, and has a better effect in metallocene catalytic systems. The synthesis of this type of compound can be obtained by reacting tris(pentafluorophenyl)borane as a raw material with organometallic compounds such as pentafluorophenyllithium in an ether-containing organic medium (Organometallics, 2004, 23:1459-1460; Inorganic Che...

Claims

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Application Information

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IPC IPC(8): C07F5/02
Inventor 闾肖波赵云陈靖
Owner SHANGHAI SINOFLUORO SCI
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