Preparation of halogenated 4-aminophenols

Abstract

The present invention relates to halogenated 4-aminophenols and to halogenated 4-(phenyldiazenyl)phenols, to a process for their preparation and to the use of the halogenated 4-hydroxyphenols for preparing active ingredients, especially in pharmaceuticals and agrochemicals.

1 . A compound of the formula (I): 
       
         
           
           
               
               
           
         
         wherein 
         m is 0, 1, 2 or 3 and 
         n is 1, 2, 3 or 4, 
         m+n is a maximum of 4, and 
         R 1  is hydrogen, C 1 -C 12 -alkyl or C 5 -C 15 -arylalkyl and 
         R 2  is in each case independently C 1 -C 12 -fluoroalkyl, C 1 -C 12 -fluoroalkylthio or C 1 -C 12 -fluoroalkoxy and 
         Hal is in each case independently bromine, chlorine or fluorine; 
         wherein the compound excludes a compound selected from the group consisting of 4-amino-3,5-difluorophenol, 4-amino-2,5-difluorophenol, 4-amino-2,6-difluorophenol, 4-amino-2-chloro-6-fluorophenol, 4-amino-2-chloro-3-fluorophenol, 4-amino-2-chloro-5-fluorophenol, 4-amino-2-bromo-5-fluorophenol, 4-amino-2-fluorophenol, 4-amino-3-fluorophenol, 4-amino-2-(trifluoromethyl)phenol, 4-amino-5-chloro-2-(trifluoromethyl)phenol, 4-amino-2-chloro-6-(trifluoromethyl)phenol ot 4-amino-3-(trifluoromethyl)phenol, and combinations thereof. 
       
     
     
         2 . A compound of the formula (V), 
       
         
           
           
               
               
           
         
         wherein 
         R 2  is in each case independently C 1 -C 12 -fluoroalkyl, C 1 -C 12 -fluoroalkylthio or C 1 -C 12 -fluoroalkoxy, 
         R 3  is in each case independently fluorine, chlorine, bromine, iodine, cyano, thiocyanato, hydroxysulphonyl or alkali metal salts thereof, nitro, C 1 -C 12 -alkyl, C 1 -C 12 -fluoroalkyl, C 1 -C 12 -fluoroalkyoxy, C 1 -C 12 -fluoroalkylthio, C 1 -C 12 -alkoxy, C 1 -C 12 -alkoxycarbonyl, di(C 1 -C 12 -alkyl)amino, C 4 -C 14 -aryl or C 5 -C 15 -arylalkyl, and 
         Hal is in each case independently bromine, chlorine or fluorine, 
         m is 0, 1, 2 or 3 and 
         n is 1, 2, 3 or 4, 
         where the sum of 
         m+n is a maximum of 4; and 
         wherein the compound of formula (V) excludes a compound selected from the group consisting of 3,5-difluoro-4-phenylazophenol, 3-fluoro-4-phenylazophenol, 3-fluoro-4-(4′-nitrophenylazo) phenol, 3-fluoro-4-(3′-nitrophenylazo)phenol, 3-fluoro-4-(4′-thiocyanatophenylazo)phenol, 3-fluoro-4-(4′-sulphophenylazo)phenol, ethyl 4-(2′-fluoro-4′-hydroxyphenylazo)benzoate, 2-fluoro-4-(4′-fluorophenylazo) phenol, 2-fluoro-4-(3′-fluorophenylazo)phenol, 2-fluoro-4-(4′-sulphophenylazo)phenol, ethyl 4-(3′-fluoro-4′-hydroxyphenylazo)benzoate, 2,3-difluoro-4-(4′-iodophenylazo) phenol, 2,3-difluoro-4-(4′-sulphophenylazo) phenol and 2,6-difluoro-4-(2′-bromophenylazo)phenol, 3-(trifluoromethyl)-4-(phenylazo)phenol and 3-(trifluoromethyl)-4-(4′-sodium sulphonate phenylazo)phenol, and combinations thereof.