US 2026/0265187 A1Published application

Method for preparing arylvinylsulphones

AssigneeKemira Oyj

InventorYogesh Laxman BOROLE

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Abstract

A method for preparing arylvinylsulphones comprises reacting an aryl sulphonyl halide with a reactive solvent selected from (meth)acrylonitrile or alkyl (meth)acrylate in the presence of a Cu(I) catalyst in a first reaction mixture to form an intermediate product, wherein the Cu(I) catalyst is uncomplexed. Unreacted reactive solvent is separated from the first reaction mixture to form a second mixture. A low polarity solvent is added to the second mixture to precipitate the Cu(I) catalyst and dissolve the intermediate product to form a third reaction mixture. A base is added to the third reaction mixture, wherein the intermediate product undergoes a base-catalysed elimination of the halogen atom from the intermediate product to form an arylvinylsulphone compound preferably under cooling. The arylvinylsulphone compound, is separated from the third reaction mixture.

Claims20

Dependent claims

A method for preparing a compound of Formula (I):

wherein
R1, R2, and R3 independently represent a hydrogen atom;
a halogen atom;
a hydroxy group;
an alkyl group;
a hydroxy alkyl group;
a haloalkyl group;
an alkoxy group having 1 to 4 carbon atoms;
an acyl group;
an amino group;
an alkylamino group or an acylamido group having 1 to 10 carbon atoms;
A represents a hydrogen atom;
a C1-C5 alkyl group;
or an alkoxycarbonyl group;
B represents a nitrile group, a carboxylic acid group, a carboxylic acid ester group or a carboxylic acid amide group;
the method comprising steps of:
(a) reacting an aryl sulphonyl halide with a reactive solvent selected from (meth)acrylonitrile or alkyl (meth)acrylate in the presence of a Cu(I) catalyst in a first reaction mixture to form an intermediate product, wherein the Cu(I) catalyst is uncomplexed;
(b) separating unreacted reactive solvent from the first reaction mixture to form a second mixture;
(c) adding a low polarity solvent to the second mixture to precipitate the Cu(I) catalyst and dissolve the intermediate product to form a third reaction mixture;
(d) adding a base to the third reaction mixture, wherein the intermediate product undergoes a base-catalysed elimination of the halogen atom from the intermediate product to form the compound according to Formula (I), preferably under cooling;
and
(e) separating the compound according to Formula (I) from the third reaction mixture.

19 more elements

Dependencies are inferred from the claim text.