The present invention provides processes for the preparation of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and novel intermediates used therein. In some embodiments the 3, 5-Dihydroxy-4-isopropyl-trans-stilbene is prepared from (E)-2-chloro-2-isopropyl-5-styrylcyclohexane-1,3-dione. Also disclosed are crystal forms of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and pharmaceutical compositions comprising same.

Disclosed herein are processes for preparing certain intermediates useful in the synthesis of 3-fluoro-5-(((1S,2aR)-1,3,3,4,4-pentafluoro-2a-hydroxy-2,2a,3,4-tetrahydro-1H-cyclopenta[cd]inden-7-yl)oxy)benzonitrile or a pharmaceutically acceptable salt thereof.

Disclosed herein are processes for preparing certain intermediates useful in the synthesis of 3-fluoro-5-(((1S,2aR)-1,3,3,4,4-pentafluoro-2a-hydroxy-2,2a,3,4-tetrahydro-1H-cyclopenta[cd]inden-7-yl)oxy)benzonitrile or a pharmaceutically acceptable salt thereof.

Disclosed herein are processes for preparing certain intermediates useful in the synthesis of 3-fluoro-5-(((1S,2aR)-1,3,3,4,4-pentafluoro-2a-hydroxy-2,2a,3,4-tetrahydro-1H-cyclopenta[cd]inden-7-yl)oxy)benzonitrile or a pharmaceutically acceptable salt thereof.

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.

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.

Disclosed herein are embodiments of a method for making substituted compounds with specific and selectable regiochemistry. Also disclosed are compounds made by the method. The method may comprise contacting a compound having a formula I

##STR00001##

with a compound according to formula II

##STR00002##

in the presence of a Lewis acid to form a phenol compound according to formula III and/or a benzofuranone compound according to formula IV

##STR00003##

Disclosed herein are embodiments of a method for making substituted compounds with specific and selectable regiochemistry. Also disclosed are compounds made by the method. The method may comprise contacting a compound having a formula I

##STR00001##

with a compound according to formula II

##STR00002##

in the presence of a Lewis acid to form a phenol compound according to formula III and/or a benzofuranone compound according to formula IV

##STR00003##

Disclosed is a method for synthesizing N-(phenylsulfonyl)benzamide compound and intermediate thereof. The method comprises a method for synthesizing a compound 1, comprising conducting a Buchwald-Hartwig coupling reaction as shown below with compound A and compound B in a solvent and in the presence of a base and a palladium catalyst to obtain the compound 1; wherein R is C.sub.1-C.sub.8 alkyl. The present disclosure synthesizes three intermediate compounds required by the target compound and their preparation methods for the first time. Using the method disclosed in the present disclosure to synthesize the target compound 3 has the advantages of high yield, good purity, easy-to-obtain reaction raw materials, suitable for industrial production.

##STR00001##