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US 10,093,634 B2Granted
Process for the preparation of substituted phenoxyphenyl ketones
AssigneeBASF Agro B.V.
InventorsUwe Josef Vogelbacher, Joachim Gebhardt, Michael Rack, Roland Goetz, Stefan Fuelster
Life of this patent
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Abstract
The present invention relates to a process for the preparation of the ketone compounds (IA) and their use as intermediates for the preparation of triazole fungicides.
Claims10
A process for the preparation of the ketone compounds (IA)
- comprising the following steps:
- reacting a compound of the formula (III)
- with R′—Mg-Hal (IV) or Mg and R1C(═O)Cl (V) in the presence of a Cu(I)-catalyst in an amount of 0.005 to 0.065 mole equivalents per 1 mole of compound (III), to result in compounds II
- wherein the compound of the formula (III) is reacted with R′—Mg-Hal (IV) in the absence of or essentially without AlCl3;
- and
- (ii) reacting compound (II) as defined in step (i) with a phenol derivative of formula (VI)
- in the presence of a base if R″ is hydrogen;
- wherein the variables are defined as follows:
- X is F or Cl;
- R1 is C1-C6-alkyl or C3-C8-cycloalkyl;
- and
- R4 is F or Cl;
- R′ is C1-C4-alkyl or C3-C6-cycloalkyl;
- Hal is halogen;
- and
- R″ is hydrogen or an alkali metal cation.
13 more elements
A process for the preparation of triazole compounds of the formula (IC)
- wherein
- R1 is C1-C6-alkyl or C3-C8-cycloalkyl;
- R2 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, phenyl, phenyl-C1-C4-alkyl, phenyl-C2-C4-alkenyl or phenyl-C2-C4-alkynyl;
- wherein the aliphatic moieties of R2 are not further substituted or do carry one, two, three or up to the maximum possible number of identical or different groups R12a which independently are selected from:
- halogen, OH, CN, nitro, C1-C4-alkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and C1-C4-halogenalkoxy;
- wherein the cycloalkyl and/or phenyl moieties of R2 are not further substituted or do carry one, two, three, four, five or up to the maximum number of identical or different groups R12b which independently are selected from:
- R12b halogen, OH, CN, nitro, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-halogenalkyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and C1-C4-halogenalkoxy;
- and
- R4 is F or Cl;
- comprising the following steps:
- (i) reacting a compound of the formula (III)
- with R′—Mg-Hal (IV) or Mg and R1C(═O)C1 (V) in the presence of a Cu(I)-catalyst in an amount of 0.005 to 0.065 mole equivalents per 1 mole of compound (III), to result in compounds II
- wherein the compound of the formula (III) is reacted with R′OMgOHal (IV) in the absence of or essentially without AlCl3;
- (ii) reacting compound (II) as defined in step (i) with a phenol derivative of formula (VI)
- in the presence of a base if R″ is hydrogen;
- wherein the variables are defined as follows:
- X is F or Cl;
- R1 is C1-C6-alkyl or C3-C8-cycloalkyl;
- and
- R4 is F or Cl;
- R′ is C1-C4-alkyl or C3-C6-cycloalkyl;
- Hal is halogen;
- and
- R″ is hydrogen or an alkali metal cation;
- to result in compounds of the formula (IA)
- (iii) reacting a ketone of the formula (IA) as defined in step (ii) to oxiranes (IB);
- and
- (iv) reacting the oxirane (IB) as defined in step (iii) with 1H-1,2,4-triazole in the presence of a base to obtain compounds (IC), wherein R2 is hydrogen (compounds IC-1);
- and, for obtaining compounds wherein R2 is different from hydrogen:
- (v) derivatizing the compound of formula (IC-1) as defined in step (iv) under basic conditions with R2-LG, wherein LG is a nucleophilically replaceable leaving group;
- to result in compounds (IC-2).
28 more elements
Dependencies are inferred from the claim text.