Method of producing...

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 261/04 (2006.01)

Patent

CA 2351466

The invention relates to a novel method of producing the compounds of formula (I) wherein the substituents have the following meanings: n is 0,1 or 2; R1, R2 represent C1-C6-alkyl; R3, R4, R5 are hydrogen, C1-C6-alkyl or R4 and R5 together form a bond; R6 is C1, Br. Said method comprises the following steps: a synthesis sequence starting from 1,2-dialkylbenzenes of formula (II); halogenation to form 3,6-dihalogen-1,2-dialkylbenzenes; haloalkylation to form benzyl bromides; oxidation to form benzaldehydes; reaction with alkenes to form isoxazoles; reaction to form thioethers and optionally oxidation to form sulfenyl or sulfonyl derivatives of formula (I).

L'invention concerne un nouveau procédé permettant de produire des composés correspondant à la formule (I), dans laquelle les substituants ont les significations suivantes: n vaut 0,1 ou 2; R?1¿, R?2¿ représentent alkyle C¿1?-C¿6?; R?3¿, R?4¿, R?5¿ représentent hydrogène, alkyle C¿1?-C¿6?, ou bien R?4¿ et R?5¿ forment ensemble une liaison; et R?6¿ représente Cl, Br. Ledit procédé comprend les étapes suivantes: séquence de synthèse à partir de 1,2-dialkylbenzène correspondant à la formule (II); halogénation consécutive pour former des 3,6-dihalogéno-1,2-dialkylbenzènes; halogénoalkylation pour former des bromures benzyliques; oxydation pour former des benzaldéhydes; oximation; réaction avec des alcènes pour former des isoxazoles; transformation en thioéthers; et, éventuellement, oxydation pour former des dérivés sulfényle ou sulfonyle correspondant à la formule (I).

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