Nippon Shokubai Co., Ltd.

Other

Fujisawa Pharmaceutical Company, Ltd.

Nippoh Chemicals Co., Ltd.

Hitoshi Mitsui

Ikuyo Ikeno

Toshiya Iida

Naoko Yamamoto

Tsunemasa Ueno

Toshimitsu Moriguchi

Ikuyo Katsumi

Naoko Hirano

Yoshinari Sato

Seiichiro Tabuchi

Yukiko Ariyoshi

Kazuo Sakane

Yuichiro Kinoshita

Kazuya Nakagawa

Ilhyong Ryu

Takahide Fukuyama

Yuichi Satoh

Kenji Sonobe

Provided is a method for producing an imide ether compound in high yield. The method is characterized in that a nitrile compound, an alcohol, and a hydrogen halide are continuously introduced into a flow reaction device comprising a mixer and a flow reactor, to be subjected to a reaction. Because a reaction proceeds in a ratio of 1:1 by a flow reactor, selectivity is improved and generation of by-products is decreased, and thus an imide ether compound can be efficiently produced.

Method for producing imide ether compound

Fluoroaryl magnesium halide is reacted with a boron compound so that a molar ratio of the fluoroaryl magnesium halide to the boron compound is not less than 3.0 and not more than 3.7, so as to produce a tetrakis (fluoroaryl) borate.magnesium compound. With this method, there occurs no hydrogen fluoride which corrodes a producing apparatus and requires troublesome waste water treatment.

Method for producing tetrakis (fluoroaryl) borate-magnesium compound

After a fluoroaryl borane derivative is precipitated from a solution containing the fluoroaryl borane derivative, a bis (fluoroaryl) borane derivative, and a hydrocarbon solvent and is subjected to first filtration so that the fluoroaryl borane derivative is isolated, a filtrate that has been obtained by the first filtration is cooled and the bis (fluoroaryl) borane derivative is separated and is subjected to second filtration so that the bis (fluoroaryl) borane derivative is isolated. In a case where the solution contains fluorobenzene, the solution is concentrated, so that the fluorobenzene is removed. Thus, it is possible to provide the high-purity fluoroaryl borane derivative and bis (fluoroaryl) borane derivative having no impurity with ease and at a low cost.

Method for purifying fluoroaryl borane derivative and bis (fluoraryl) borane derivative

Bis(fluoroaryl)borane derivative is produced by reacting tris(fluoroaryl)borane with a compound, such as water, ethanol, ammonia and the like, in a hydrocarbon solvent at a molar ratio raging from 1:0.9 to 1:1.1. It is more preferable that the reaction is carried out while the hydrocarbon solvent is distilled off. It is more preferable that hydrocarbon solvent is substantially an aliphatic hydrocarbon solvent. With this arrangement, it is possible to provide a method for producing and isolating the bis(fluoroaryl)borane derivative of a high purity, with ease and at a low cost.

Process for preparing bis(fluoroaryl)boron derivatives

Process for preparing a tetrakis(fluoroaryl) borate derivative

PURIFYING PROCESS OF TETRAKIS (FLUOROARYL) BORATE&middot;MAGNESIUM HALIDE, TETRAKIS (FLUOROARYL) BORATE&middot;ETHER COMPLEX AND PRODUCING PROCESS OF THE SAME, AND PRODUCING PROCESS OF TETRAKIS (FLUOROARYL) BORATE DERIVATIVE

In a method for purifying a fluoroaryl metal compound of the present invention, magnesium halide is precipitated and removed from a solution containing the fluoroaryl metal compound, the magnesium halide, and an ether solvent. Or, the magnesium halide is removed by treating the solution with an acid. Examples of the method include: a method in which a solvent which has a boiling point higher than that of the ether solvent contained in the solution and which does not dissolve the magnesium halide is heated to a temperature higher than the boiling point of the ether solvent, then the ether solvent is distilled out with the solution being added to the solvent; and a method in which the solution and an aqueous solution containing an acid are mixed and stirred, then allowed to stand so as to be separated into an organic layer containing the fluoroaryl metal compound and an aqueous layer containing the magnesium halide and the acid. In this manner, a highly pure fluoroaryl metal compound having no impurities can be purified easily and inexpensively.

Method for purifying fluoroaryl metal compound

A method for easily and inexpensively producing and purifying a fluoroaryl metal compound such as bis(pentafluorophenyl)dialkyltin which is less colored and has no impurities is provided. Hydrocarbon magnesium halide is reacted with fluoroaryl halide in a solvent including an ether solvent so as to obtain fluoroaryl magnesium halide, which is then reacted with an organic metal compound so as to produce a fluoroaryl metal compound. Tin is more preferable as a metal atom included in the organic metal compound. As for the ether solvent, chain ether solvents are preferable, more specifically, diisopropyl ether, dibutyl ether, and t-butylmethyl ether are more preferable. Besides, it is preferable that magnesium halide, which is a by-product of the fluoroaryl metal compound, is precipitated and removed, or treated with an acid.

Method for producing fluoroaryl metal compound

Handling method of (fluoroaryl) borane compound and preparing method of hydrocarbon solution

PURIFYING PROCESS OF TETRAKIS(FLUOROARYL)BORATE.MAGNESIUM HALIDE, TETRAKIS(FLUOROARYL)BORATE&middot;ETHER COMPLEX AND PRODUCING PROCESS OF THE SAME, AND PRODUCING PROCESS OF TETRAKIS(FLUOROARYL)BORATE DERIVATIVE

Benzodiazepine derivatives of the formula:

1,4-benzodiazepinones and their uses as CCK antagonists

A solution containing an organic solvent and a compound including impurities, represented by, for example, general formula (1)

Method for purifying tetrakis(fluoroaryl)borate compounds or tris(fluoroaryl)borate compounds

In order to provide a method of safely, efficiently, and industrially manufacturing fluoroaryl magnesium halide containing no impurities, such as coloring components, by a relatively gradual reaction compared with the conventional reactions, and a method of readily and efficiently manufacturing a highly-pure fluoroaryl borane derivative, fluoroaryl magnesium halide expressed by General Formula (1):

Method for manufacturing fluoroaryl magnesium halide

Tetrakis(fluoroaryl)borate.magnesium halide (Ar,BMgX) expressed by General Formula (1):

Method for purifying tetrakis (fluoroaryl) borate/magnesium halide, tetrakis (fluoroaryl) borate/ether complex and process for preparing the same, and process for preparing tetrakis (fluoroaryl) borate derivative

A (fluoroaryl)borane compound expressed by General Formula (1): ##STR1## where each of R.sub.1 -R.sub.5 represents a hydrogen atom, a fluorine atom, a hydrocarbon group, or an alkoxy group, provided that at least one of R.sub.1 -R.sub.5 represents a fluorine atom, X represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and n represents 2 or 3, is stabilized by letting inorganic metal salts having a fluorine atom coexist with the (fluoroaryl)borane compound in a hydrocarbon solution. After the hydrocarbon solution is concentrated in the presence of the inorganic metal salts, the inorganic metal salts are removed and the fluoroaryl)borane compound is crystallized. Consequently, it has become possible to provide a method of stabilizing a (fluoroaryl)borane compound by suppressing the decomposition reaction while the solution is heated and concentrated, stored (preserved), or transported/transferred, and a crystallizing method of isolating highly-pure crystals (powders) of the (fluoroaryl)borane compound efficiently.

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Kitakatsuragi-gun, Japan

Hitoshi Mitsui