The present invention provides a method for producing a benzaldehyde in which an amino group is bonded in the 2 position, a halogeno group or an alkoxy group is bonded in the 3 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of the 4, 5, and 6 positions, the method including: preparing a benzaldehyde in which a halogeno group or an alkoxy group is bonded in the 3 position, a hydrogen atom is bonded in the 2 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of the 4, 5, and 6 positions so that a lithiation reaction is most active at the 2 position; acetal-protecting a formyl group in the benzaldehyde; sequentially performing lithiation, azidation, and amination of the 2 position; and the performing acetal deportection.

The present invention provides a method for producing a benzaldehyde in which an amino group is bonded in the 2 position, a halogeno group or an alkoxy group is bonded in the 3 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of the 4, 5, and 6 positions, the method including: preparing a benzaldehyde in which a halogeno group or an alkoxy group is bonded in the 3 position, a hydrogen atom is bonded in the 2 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of the 4, 5, and 6 positions so that a lithiation reaction is most active at the 2 position; acetal-protecting a formyl group in the benzaldehyde; sequentially performing lithiation, azidation, and amination of the 2 position; and the performing acetal deportection.

Provided herein are halogenated ether compounds of Formula (I), Formula (II), or Formula (III):

##STR00001##

Also provided are electrolytes comprising one or more compounds of Formula (I), Formula (II), or Formula (III) and electrochemical cells comprising electrolytes comprising one or more compounds of Formula (I), Formula (II), or Formula (III).

Provided herein are halogenated ether compounds of Formula (I), Formula (II), or Formula (III):

##STR00001##

Also provided are electrolytes comprising one or more compounds of Formula (I), Formula (II), or Formula (III) and electrochemical cells comprising electrolytes comprising one or more compounds of Formula (I), Formula (II), or Formula (III).

A composition in which a fluorine-containing monomer is stabilized, a method for stabilizing a fluorine-containing monomer, and the like are provided. The composition includes a fluorine-containing monomer (M) and a polycyclic aromatic compound (B). The fluorine-containing monomer (M) includes at least one monomer selected from a compound represented by formula (M1), a compound represented by formula (M2), and a compound represented by formula (M3). The polycyclic aromatic compound (B) includes a compound represented by formula (B1).

##STR00001##

R.sup.1-R.sup.10 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, and R.sup.11-R.sup.18 each independently represent a hydrogen atom or an alkyl group, however, excluding an embodiment in which R.sup.17 represents a tert-butyl group, with R.sup.11-R.sup.16 and R.sup.18 being a hydrogen atom.

A composition in which a fluorine-containing monomer is stabilized, a method for stabilizing a fluorine-containing monomer, and the like are provided. The composition includes a fluorine-containing monomer (M) and a polycyclic aromatic compound (B). The fluorine-containing monomer (M) includes at least one monomer selected from a compound represented by formula (M1), a compound represented by formula (M2), and a compound represented by formula (M3). The polycyclic aromatic compound (B) includes a compound represented by formula (B1).

##STR00001##

R.sup.1-R.sup.10 each independently represent a fluorine atom, a perfluoroalkyl group, or a perfluoroalkoxy group, and R.sup.11-R.sup.18 each independently represent a hydrogen atom or an alkyl group, however, excluding an embodiment in which R.sup.17 represents a tert-butyl group, with R.sup.11-R.sup.16 and R.sup.18 being a hydrogen atom.

The coupling of aryl, heteroaryl, and vinyl halides with ,-difluoroketones or silyl ethers or siylenol ethers of ,-difluoroketones and ,-difluoroamides and esters are described. Further derivatization of the coupling products (such as ketone cleavage and Baeyer-Villiger oxidation) is also described.

The coupling of aryl, heteroaryl, and vinyl halides with ,-difluoroketones or silyl ethers or siylenol ethers of ,-difluoroketones and ,-difluoroamides and esters are described. Further derivatization of the coupling products (such as ketone cleavage and Baeyer-Villiger oxidation) is also described.

An object of the present disclosure is to provide a novel method for producing a 1,3-dioxolane compound having a 2-(difluoromethylene) structure (e.g., 2-(difluoromethylene)-4,4,5-trifluoro-5-(trifluoromethyl)-1,3-dioxolane) from a corresponding carboxylic acid salt, the method suppressing the production of HF adducts (e.g., 2-hydro-perfluoro(2,4-dimethyl-1,3-dioxolane)) as by-products. The present disclosure relates to a method for producing a compound represented by formula (1), the method comprising the following steps A, B, C, and D: step A of reacting a compound represented by formula (2) with at least one base selected from the group consisting of hydroxides, carbonates, and alkoxides of alkali metals and alkaline earth metals to produce a compound represented by formula (3), thereby obtaining a reaction product having a pH range of more than 11.0; step B of adding carbon dioxide gas to the reaction product obtained in step A, or a liquid obtained by mixing the reaction product with water, to adjust the pH to 6.0 to 11.0, thereby obtaining a pH-adjusted liquid; step C of concentrating the pH-adjusted liquid obtained in step B to obtain a concentrate; and step D of heating the concentrate obtained in step C to thermally decompose the compound represented by formula (3), thereby producing the compound represented by formula (1):

##STR00001##

wherein R.sup.1 to R.sup.4 are each independently a fluorine atom or a C1-C7 fluoroalkyl group optionally containing ethereal oxygen, X is a hydroxy group, a fluorine atom, a chlorine atom, or a C1-C3 alkoxy group in which one or more hydrogen atoms are optionally replaced by fluorine atoms, and M is an alkali metal atom or an alkaline earth metal atom.

An object of the present disclosure is to provide a novel method for producing a 1,3-dioxolane compound having a 2-(difluoromethylene) structure (e.g., 2-(difluoromethylene)-4,4,5-trifluoro-5-(trifluoromethyl)-1,3-dioxolane) from a corresponding carboxylic acid salt, the method suppressing the production of HF adducts (e.g., 2-hydro-perfluoro(2,4-dimethyl-1,3-dioxolane)) as by-products. The present disclosure relates to a method for producing a compound represented by formula (1), the method comprising the following steps A, B, C, and D: step A of reacting a compound represented by formula (2) with at least one base selected from the group consisting of hydroxides, carbonates, and alkoxides of alkali metals and alkaline earth metals to produce a compound represented by formula (3), thereby obtaining a reaction product having a pH range of more than 11.0; step B of adding carbon dioxide gas to the reaction product obtained in step A, or a liquid obtained by mixing the reaction product with water, to adjust the pH to 6.0 to 11.0, thereby obtaining a pH-adjusted liquid; step C of concentrating the pH-adjusted liquid obtained in step B to obtain a concentrate; and step D of heating the concentrate obtained in step C to thermally decompose the compound represented by formula (3), thereby producing the compound represented by formula (1):

##STR00001##

wherein R.sup.1 to R.sup.4 are each independently a fluorine atom or a C1-C7 fluoroalkyl group optionally containing ethereal oxygen, X is a hydroxy group, a fluorine atom, a chlorine atom, or a C1-C3 alkoxy group in which one or more hydrogen atoms are optionally replaced by fluorine atoms, and M is an alkali metal atom or an alkaline earth metal atom.