Verfahren zur Herstellung von halogenhaltigen 4-Aminophenolen

• Main Authors: MARHOLD, ALBRECHT, JOSCHEK, JENS-PETER, PEILSTOECKER, KAREN
• Format: Patent
• Language: German
• Published: 31.03.2005
• Edition: 7
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY

Die vorliegende Erfindung betrifft halogenierte 4-Aminophenole sowie halogenierte 4-(Phenyldiazenyl)phenole, ein Verfahren zu deren Herstellung sowie die Anwendung der halogenierten 4-Hydroxyphenole zur Herstellung von Wirkstoffen insbesondere in Arzneimitteln und Agrochemikalien. Production of 4-aminophenol derivatives (I) comprises converting an aniline (II) to a diazonium salt (III), reacting (III) with a phenol (IV) in the presence of a base to give a phenylazophenol (V), and reacting (V) with a reducing agent and optionally O-alkylating the product. Production of 4-aminophenol derivatives of formula (I) comprises converting an aniline of formula (II) to a diazonium salt of formula (III), reacting (III) with a phenol of formula (IV) in the presence of a base to give a phenylazophenol of formula (V), and reacting (V) with a reducing agent and optionally O-alkylating the product: [Image] m : 0-3; n : 1-4; m+n : 4 or less; R 1>H, 1-12C alkyl or 5-15C aralkyl; R 2>1-12C fluoroalkyl, 1-12C fluoroalkylthio or 1-12C fluoroalkoxy; Hal : Br, Cl or F; R 3>halo, CN, SCN, SO 3M, NO 2, 1-12C alkyl, 1-12C fluoroalkyl, 1-12C fluoroalkylthio,1-12C fluoroalkoxy, 1-12C alkoxy, 1-12C alkoxycarbonyl, di(1-12C alkyl)amino, 4-14C aryl or 5-15C aralkyl; M : H or alkali metal; p : 0-3; An : an anion. Independent claims are also included for: (1) compounds (I) other than 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-5-chloro-2-(trifluoromethyl)phenol, 4-amino-2-chloro-6-(trifluoromethyl)phenol and (it is stated) 4-amino-2-(trifluoromethyl)phenol and 4-amino-3-(trifluoromethyl)phenol; compounds (V) other than 3,5-difluoro-4-phenylazo-phenol, 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'-sulfophenylazo)-phenol, 4-(2'-fluoro-4'-hydroxyphenylazo)benzoic acid ethyl ester, 2-fluoro-4-(4'-fluorophenylazo)-phenol, 2-fluoro-4-(3'-fluorophenylazo)-phenol, 2-fluoro-4-(4'-sulfophenylazo)-phenol, 4-(3'-fluoro-4'-hydroxyphenylazo)benzoic acid ethyl ester, 2,3-difluoro-4-(4'-iodphenylazo)-phenol; 2,3-difluoro-4-(4'sulfophenylazo)-phenol, 2,6-difluoro-4-(2'-bromphenylazo)-phenol and (it is stated) 3-(trifluoromethyl)-4-(phenylazo)-phenol and 3-(trifluoromethyl)-4-(4'-sodiumsulfonatophenylazo)-phenol.