Diaryl sulfone compound, and manufacturing method for same

A method for producing a diaryl sulfone compound represented by Formula (1-1-a):

• wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl or halogen;
• and R6 is C1-4 alkylene;
• the method comprising reacting a 4,4′-dimercaptodiaryl sulfone compound represented by Formula (2):
• wherein R1 to R4, R1′ to R4′, and R6 are as defined above;
• with a halide represented by Formula (3):
• wherein R6 is as defined above and X is halogen;
• in a solvent in the presence of at least one catalyst selected from the group consisting of lithium chloride and lithium bromide to produce a compound represented by Formula (4):
• wherein R1 to R4, R1′ to R4′, R6, and X are as defined above;
• and reacting the resulting compound with a base to perform a dehydrohalogenation reaction.

A method for producing diaryl sulfone compound represented by Formula (1-1-b):

• wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl, or halogen;
• and R6 represents C1-4 alkylene;
• the method comprising reacting a compound represented by Formula (1-1-a):
• wherein R1 to R4, R1′ to R4′, and R6 are as defined above;
• with at least one compound selected from the group consisting of thiourea and thiocyanates, in an organic solvent.

A method for producing a diaryl sulfone compound represented by Formula (1-2):

• wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl, or halogen;
• and R7 represents C2-5 alkenyl;
• the method comprising reacting a salt of 4,4′-dimercaptodiaryl sulfone represented by Formula (2-1):
• wherein R1 to R4, R1′ to R4′, and R7 are as defined above;
• and M represents a cation moiety of a base;
• with a halide represented by Formula (5):
• wherein R7 is as defined above, and X represents halogen.

A method for producing a dimercaptodiaryl sulfone compound represented by Formula (2):

• wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl, or halogen;
• the method comprising reacting a dimethylthiodiaryl sulfone compound represented by Formula (6):
• wherein R1 to R4 and R1′ to R4′ are as defined above;
• with at least one halogenating agent selected from the group consisting of chlorine, sulfuryl chloride, phosphorus pentachloride, phosphorous trichloride, hypochlorous acid and bromine to obtain a diaryl sulfone compound represented by Formula (7):
• wherein R1 to R4 and R1′ to R4′ are as defined above;
• X represents halogen;
• and m and n each represents an integer of 1 to 3;
• and subjecting the resulting compound to hydrolysis.