FLUORIDE CONTAINING AROMATIC COMPOUNDS

Preparation of fluorinated 2-hydroxyphenylacetonitrile derivatives (I) comprises reacting a fluorinated phenol compound (II) with formaldehyde and amine compound (III), reacting the obtained tertiary benzylamine compound (IV) with an acid anhydride (V) and reacting the obtained benzyl ester compound...

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Bibliographic Details
Main Authors MARHOLD, ALBRECHT, PLESCHKE, AXEL, GIFFELS, GUIDO, PEILSTOECKER, KAREN
Format Patent
LanguageEnglish
French
German
Published 02.03.2005
Edition7
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
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Summary:Preparation of fluorinated 2-hydroxyphenylacetonitrile derivatives (I) comprises reacting a fluorinated phenol compound (II) with formaldehyde and amine compound (III), reacting the obtained tertiary benzylamine compound (IV) with an acid anhydride (V) and reacting the obtained benzyl ester compound (VI) with a cyanide. Preparation of fluorinated 2-hydroxyphenylacetonitrile derivatives of formula (I) comprises: (a) reacting a fluorinated phenol compound (II) with formaldehyde and an amine compound of formula NHR3R4 (III); (b) reacting the obtained tertiary benzylamine compound of formula (IV) with an acid anhydride compound of formula R5C(O)OC(O)R5 (V); and (c) reacting the obtained benzyl ester compound of formula (VI) with a cyanide. R1 = 1-12C alkyl, free or protected formyl, chloro, bromo, A-B'-D-E or A-E; A = 1-8C alkylene or is absent; B' = oxygen, sulfur, NR2 or is absent; R2 = H or 1-8C alkyl; D = carbonyl; E = 1-8C alkyl, 1-8C alkoxy, mono- or di-1-8C alkylamino or 4-12C cyclic amino; n = 0 to 4-m; RF = F, 1-12C fluoroalkyl, 1-12C fluoroalkoxy or 1-12C fluoroalkylthio; m = 1-3; R3, R4 = 1-8C alkyl or NR3R4 = 4-12C cyclic amino, and R5 = H, 1-12C alkyl, 2-12C alkenyl, 5-14C aryl or 6-15C aralkyl. Independent claims are also included for: (1) preparation of (I) which comprises step (c) per se; (2) preparation of (VI) which comprises step (b) per se; (3) preparation of (IV) which comprises step (a) per se; (4) new compounds (I); (5) new compounds (IV), excluding 2-hydroxy-5-fluoro-N,N-dimethylbenzylamine; (6) new compounds (VI), excluding 2-acetoxy-5-fluorobenzyl acetate, and (7) compounds of formula (VIIIa). R6 = 1-12C alkyl, 5-14C aryl or 6-15C aralkyl.
Bibliography:Application Number: EP20030026981