Mitsubishi Gas Chemical Company, Inc.

Hokkaido University

Daikin Industries, Ltd.

Other

Shoji Hara

Tsuyoshi Fukuhara

Yosuke Kishikawa

Sumi Ishihara

Toshio Hidaka

Atsushi Shirai

Takashi Namikawa

Masahiro Higashi

Takafumi Yoshimura

An object of the present invention is to provide a method for producing a fluorinated organic compound with a high yield without using carbon tetrachloride in view of the fact that the production of a fluorinated organic compound with a sufficient yield was impossible for a hitherto-known method that uses a fluorinating agent that contains IF-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent that is capable of achieving this object. The present invention provides a composition comprising (1) IFand (2) an aprotic solvent (with the proviso that carbon tetrachloride is excluded), wherein the aprotic solvent is contained in an amount within a range of 50 mass ppm to 20 mass %.

Composition, fluorinating reagent, and method for producing fluorinated organic compound

An object of the present invention is to provide a novel substance that has a high reactivity as a fluorinating agent, is effectively used in various fluorination reactions, and is safely handled even in air. As the solution for achieving this object, the present invention provides a complex obtained by reacting bromine trifluoride with at least one metal halide selected from the group consisting of halogenated metals and halogenated hydrogen metals in a nonpolar solvent. This complex serves as a fluorinating agent that provides excellent fluorination performance and that is stable in air.

Fluorinating agent

Object: An object of the present invention is to provide a method for producing, with a high yield, a fluorinated organic compound, the fluorinated organic compound having not been produced with a sufficient yield by a conventional method for producing a fluorinated organic compound using a fluorinating agent containing IF-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent. Means for achieving the object: A method for producing a fluorinated organic compound comprising step A of fluorinating an organic compound by bringing the organic compound into contact with (1) IF-pyridine-HF and (2) at least one additive selected from the group consisting of amine hydrogen fluorides, XF (wherein Xrepresents hydrogen, potassium, sodium, or lithium), oxidizers, and reducing agents.

Method for producing fluorinated organic compound and fluorinating reagent

Provided are a fluorous-tag-introduced fluoroamine of a general formula (I), its production method, a method of fluorination of a substrate having functional group containing oxygen with the fluoroamine serving as a fluorinating agent, and a method of recovering a fluorous-tag-introduced amide after the fluorination. The fluoroamine and its production method, as well as the fluorination method with the fluoroamine and the method of recovery of a fluorous-tag-introduced amide are ecological and advantageous in industrial use, as the load for separating and collecting the product after the fluorination with the fluoroamine serving as a fluorinating agent is small. (In the formula, Ris an alkyl group or an aryl group having substituent(s) of Rf&#x2014;(CH)&#x2014;; Rf is a perfluoroalkyl group; m is from 0 to 2; Rand Reach are an alkyl group or an aryl group.)

Fluoroamine having perfluoroalkyl group, process for producing the same, method of fluorination therewith, and method of recovering amide having perfluoroalkyl group

The present invention is a method for producing a 2-oxazoline analogue or a 1,3-oxazine analogue represented by the following general formula (3) by reacting a 1,2-aminoalcohol compound or a 1,2-aminothiol compound with an &#x3b1;,&#x3b1;-dihaloamine compound. (In the formula, n represents 0 or 1, and R represents an oxygen atom or a sulfur atom. R, Rand Reach represents an atom or a group shown in Group 1 to Group 3, and Rrepresents an atom or a group shown in Group 2 or Group 3. Two or more of R, Rand Rmay be bonded to each other to form a ring. Group 1: a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a carboxyl group, a sulfonyl group, a sulfinoyl group or a sulfenyl group; Group 2: an alkyl group, which may have an arbitrary substituent, an aryl group or an aralkyl group; and Group 3: an alkyl-substituted, aryl-substituted or aralkyl-substituted oxy group, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, a thio group, a sulfonyl group, a sulfinoyl group or a sulfenyl group) 

Method for producing 2-oxazoline analogue or 1,3-oxazine analogue

A method of fluorination comprising reacting monosaccharides, oligosaccharides, polysaccharides, composite saccharides formed by bonding of these saccharides with proteins and lipids and saccharides having polyalcohols, aldehydes, ketones and acids of the polyalcohols, and derivatives and condensates of these compounds with a fluorinating agent represented by general formula (I) thermally or under irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region. In accordance with the method, the fluorination at a selected position can be conducted safely at a temperature in the range of 150 to 200&#xb0; C. where the reaction is difficult in accordance with conventional methods. The above method comprising the irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region can be applied to substrates other than saccharides. When a complex compound comprising HF and a base is reacted under irradiation with microwave, fluorination at a specific position which is difficult in accordance with conventional methods proceeds highly selectively, efficiently in a short time and safely. 

Method of fluorination

A process for producing an &#x3b1;,&#x3b1;-difluoroamine which comprises using hydrogen fluoride and a Lewis base in specific amounts in the halogen-fluorine exchange reaction using an &#x3b1;,&#x3b1;-dihaloamine as the substrate. The process can be industrially applied, enables to obtain the object compound in a short time at a great yield and can be conducted easily with excellent productivity.

Process for producing &#x3b1;, &#x3b1;-difluoroamine

A method of fluorination comprising reacting monosaccharides, oligosaccharides, polysaccharides, composite saccharides formed by bonding of these saccharides with proteins and lipids and saccharides having polyalcohols, aldehydes, ketones and acids of the polyalcohols, and derivatives and condensates of these compounds with a fluorinating agent represented by general formula (I) thermally or under irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region. In accordance with the method, the fluorination at a selected position can be conducted safely at a temperature in the range of 150 to 200&#xb0; C. where the reaction is difficult in accordance with conventional methods. The above method comprising the irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region can be applied to substrates other than saccharides 

The present invention provides a process for producing an optically active fluoro compound represented by formula (3) through reaction between a specific fluoroamine and an optically active diol; and a process for producing an optically active fluoroalcohol through hydrolysis of the optically active fluoro compound. According to the process of the present invention, such optically active fluoro compounds and optically active fluoroalcohols can be produced at high optical purity and high yield in a simple manner. Such optically active fluoroalcohols are a useful source for producing drugs, pesticides, and other functional chemicals 

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Hokkaido, Japan

Shoji Hara