An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound. The above object can be achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2):

##STR00002##

wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3):

##STR00003##

wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound. The above object can be achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2):

##STR00002##

wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3):

##STR00003##

wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

A method for producing a fluorine-containing halogenated hydrocarbon comprising reacting a chlorine-containing compound and hydrogen fluoride in a vapor phase, and a separation step of separating a reaction product containing hydrogen fluoride, hydrogen chloride, and organic matter containing the fluorine-containing halogenated hydrocarbon into multiple components, the separation step comprising: separating the reaction product into a gas phase and a liquid phase, increasing the pressure of the liquid phase and supplying the liquid phase into a distillation column, compressing the gas phase and supplying the gas phase into the distillation column, separating a first stream containing the hydrogen chloride from the top of the distillation column, and separating a second stream containing the organic matter and the hydrogen fluoride from the bottom of the distillation column. The method is for stably obtaining a target compound by preventing hydrogen fluoride contained in the outlet gas from condensing during compression.

A method for producing a fluorine-containing halogenated hydrocarbon comprising reacting a chlorine-containing compound and hydrogen fluoride in a vapor phase, and a separation step of separating a reaction product containing hydrogen fluoride, hydrogen chloride, and organic matter containing the fluorine-containing halogenated hydrocarbon into multiple components, the separation step comprising: separating the reaction product into a gas phase and a liquid phase, increasing the pressure of the liquid phase and supplying the liquid phase into a distillation column, compressing the gas phase and supplying the gas phase into the distillation column, separating a first stream containing the hydrogen chloride from the top of the distillation column, and separating a second stream containing the organic matter and the hydrogen fluoride from the bottom of the distillation column. The method is for stably obtaining a target compound by preventing hydrogen fluoride contained in the outlet gas from condensing during compression.

An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a halogenated diene represented by formula (1): A.sup.1A.sup.2C═CA.sup.3-CA.sup.4=CA.sup.5A.sup.6 [A.sup.1, A.sup.2, A.sup.5, and A.sup.6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.3 and A.sup.4 are each independently hydrogen, fluorine, or chlorine; at least one of A.sup.1 to A.sup.6 is hydrogen; at least one of A.sup.1 to A.sup.6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A.sup.7A.sup.8C═CA.sup.9X [A.sup.7 and A.sup.8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a halogenated diene represented by formula (1): A.sup.1A.sup.2C═CA.sup.3-CA.sup.4=CA.sup.5A.sup.6 [A.sup.1, A.sup.2, A.sup.5, and A.sup.6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.3 and A.sup.4 are each independently hydrogen, fluorine, or chlorine; at least one of A.sup.1 to A.sup.6 is hydrogen; at least one of A.sup.1 to A.sup.6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A.sup.7A.sup.8C═CA.sup.9X [A.sup.7 and A.sup.8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

A method for producing a fluorine-containing halogenated hydrocarbon comprising reacting a chlorine-containing compound and hydrogen fluoride in a vapor phase, and a separation step of separating a reaction product containing hydrogen fluoride, hydrogen chloride, and organic matter containing the fluorine-containing halogenated hydrocarbon into multiple components, the separation step comprising: separating the reaction product into a gas phase and a liquid phase, increasing the pressure of the liquid phase and supplying the liquid phase into a distillation column, compressing the gas phase and supplying the gas phase into the distillation column, separating a first stream containing the hydrogen chloride from the top of the distillation column, and separating a second stream containing the organic matter and the hydrogen fluoride from the bottom of the distillation column. The method is for stably obtaining a target compound by preventing hydrogen fluoride contained in the outlet gas from condensing during compression.

Provided is a method for producing a perfluoroalkylated compound at low cost, safely and with high efficiency. A method for producing a perfluoroalkylated compound, comprising reacting a bis(perfluoroalkanoyl) peroxide with a compound having a carbon-carbon unsaturated bond and/or an aromatic ring having a hydrogen atom bonded thereto in the presence of a copper catalyst.

Provided is a method for producing a perfluoroalkylated compound at low cost, safely and with high efficiency. A method for producing a perfluoroalkylated compound, comprising reacting a bis(perfluoroalkanoyl) peroxide with a compound having a carbon-carbon unsaturated bond and/or an aromatic ring having a hydrogen atom bonded thereto in the presence of a copper catalyst.

The present invention discloses a nicotinyl alcohol ether derivative, a preparation method therefor, and a pharmaceutical composition and uses thereof. Specifically, the invention relates to nicotinyl alcohol ether derivatives represented by formula (I), a pharmaceutically-acceptable salt thereof, a stereoisomer thereof, a preparation method therefor, a pharmaceutical composition containing the one or more compounds, and uses of the compounds in treating diseases related to PD-1/PD-L1 signal channels, such as cancers, infectious diseases and autoimmune diseases.

##STR00001##