Process for preparing substituted phenylisoxazoline derivatives

Patent metadata

Field	Value
Publication number	US-10189799-B2
Application number	US-201615548216-A
Country	US
Kind code	B2
Filing date	Feb 29, 2016
Priority date	Mar 5, 2015
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

The present invention relates to a process for preparing substituted phenylisoxazoline derivatives.

First claim

The invention claimed is:

1. Process for preparing one or more phenylisoxazoline derivatives of formula (I)

wherein
R 1 is methyl, bromomethyl or chloromethyl;
R 2 is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl and
R 3 is C 1 -C 4 -alkylsulphonyloxy, C 1 -C 4 -haloalkylsulphonyloxy,
wherein, in (i), a chloroxime of formula (II)

wherein R 4 is C 1 -C 12 -alkyl,
is reacted with a styrene of formula (III)

wherein R 2 and R 3 are as defined above,
in the presence of an inorganic base in an organic aprotic solvent to give the corresponding phenylisoxazoline of formula (IV)

wherein R 2 , R 3 and R 4 are as defined above,
and the latter then reacts, in (ii), with an organometallic reagent and an organic base in an organic aprotic solvent to give the ketone of formula (Ia)

wherein R 2 and R 3 are as defined above,
and then, in (iii), in the presence of a halogenating agent in a solvent, the haloketone of formula (Ib) is formed

wherein R 2 and R 3 are as defined above and
X is chlorine or bromine.

2. Process according to claim 1 , wherein
R 1 is methyl, bromomethyl, chloromethyl;
R 2 is chlorine or bromine;
R 3 is methylsulphonyloxy or ethylsulphonyloxy;
R 4 is C 1 -C 4 -alkyl and
X is chlorine or bromine.

3. Process according to claim 1 , wherein
R 1 is methyl, bromomethyl;
R 2 is chlorine;
R 3 is methylsulphonyloxy;
R 4 is methyl, ethyl and
X is bromine.

4. Process according to claim 1 , wherein, in (ii), triethylamine is used as base and methylmagnesium bromide or methylmagnesium chloride as organometallic reagent.

Assignees

• Bayer Cropscience Aktiengesellschsaft
• Bayer Cropscience Ag

Inventors

• Funke Christian
• Heinrich Jens Dietmar
• Pazenok Sergii
• Lui Norbert

Classifications

• C07D261/08 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D261/04 Primary

  having one double bond between ring members or between a ring member and a non-ring member · CPC title

• A01N43/80

  five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2 · CPC title