US 6,603,017 B2Granted

Preparation of 2-alkyl-3-(4,5-dihydroisoxazol-3-yl) halobenzenes

AssigneeBASF SE

InventorsMichael Rack, Norbert Götz, Helmut Hagen, Wolfgang von Deyn, Ernst Baumann, Rene Lochtman, Joachim Gebhardt

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Abstract

A novel process for preparing the compounds of the formula I where: n is 0, 1 or 2; R1, R2 are C1-C6-alkyl; R3, R4, R5 are hydrogen or C1-C6-alkyl, or R4 and R5 together form a bond; R6 is Cl, Br, which comprises a synthesis sequence starting from 1,2-dialkylbenzenes of the formula II with subsequent halogenation to give 3,6-dihalo-1,2-dialkylbenzenes, haloalkylation to give benzyl bromides, oxidation to give benzaldehydes, oximation, reaction with alkenes to give isoxazoles, conversion into thioethers and, if appropriate, oxidation to give sulfenyl or sulfonyl derivatives of the formula I.

Claims4

Dependent claims

A process for producing an aldehyde of formula V

wherein
R1 is a C1-C6-alkyl and
R6 is Cl or Br,
comprising
a) halogenating a 1,2-dialkylbenzene of formula II
in which the radicals R1 are identical or different and are as defined above with a halogen to give a 3,6-dihalo-1,2-dialkylbenzene of formula III
wherein R1 and R6 are as defined above,
b) reacting a 3,6-dihalo-1,2-dialkylbenzene of formula III with hydrogen peroxide and a halogenating agent to give a benzyl halide of formula IV
in which the radicals R1 and R6 are as defined above,
c) oxidyzing a benzyl halide of formula IV with an oxidizing agent to give an aldehyde of formula V
in which the substituents R1 and R6 are as defined above.

8 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/141,236Filed 9 May 2002 · division
Priority: DE 198 53 03918 Nov 1998
Published: US 2002/0156290 A124 Oct 2002
Granted: 5 Aug 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification2 codes

C07D 261/04
Not condensed with other rings: having one double bond between ring members or between a ring member and a non-ring member
C07D
Heterocyclic compounds

Family

PCT/EP99/08844Parent of this division · filed 17 Nov 1999
US 2002/0156290 A1Pre-grant publication · published 24 Oct 2002
Application09/856,037Parent of this division
US 6,548,677 B1Related patent
US 6,603,017 B2This patent

From the US filing history. Foreign family members aren’t listed.