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US 10,633,321 B2Granted
Method for producing cyclopropyl-substituted acetophenones
AssigneeBayer CropScience AG
InventorChristoph Schotes
Life of this patent
Estimating the term…
Abstract
A method is described for preparing cyclopropyl-substituted acetophenones of the general formula (I).
Claims10
A method for preparing a cyclopropyl-substituted acetophenone of formula (I),
- comprising
- a) in a first step reacting a benzylmagnesium halide or a benzylzinc halide (II) with a cyclopropyl alkyl ketone (III) to give an alcohol (IV),
- b) in a second step converting the alcohol (IV) to a halohydrin (V) by free-radical halogenation,
- c) in a third step converting the halohydrin (V) to an epoxide (VI) by addition of base,
- d) in a fourth step converting the epoxide (VI) to the cyclopropyl-substituted acetophenone (I) under thermal Lewis acid or Brønsted acid conditions,
- wherein
- R1 is chlorine, bromine, iodine, alkoxy, amino, cyano, nitro, C1-C4-alkyl or is unsubstituted phenyl or phenyl substituted by s radicals selected from the group consisting of chlorine, fluorine, methoxy and ethoxy,
- R2 is C1-C4-alkyl or is unsubstituted phenyl or phenyl substituted by s radicals selected from the group consisting of chlorine, fluorine, methoxy and ethoxy,
- s is 1, 2 or 3,
- X1, X2 are each independently chlorine, bromine or iodine.
7 more elements
A compound of formula (V),
- wherein
- R1 is chlorine, bromine, iodine, alkoxy, amino, cyano, nitro, C1-C4-alkyl or is unsubstituted phenyl or phenyl substituted by s radicals selected from the group consisting of chlorine, fluorine, methoxy and ethoxy,
- R2 is C1-C4-alkyl or is unsubstituted phenyl or phenyl substituted by s radicals selected from the group consisting of chlorine, fluorine, methoxy and ethoxy,
- s is 1, 2 or 3,
- X2 is chlorine, bromine or iodine.
2 more elements
A compound of formula (VI),
- wherein
- R1 is chlorine, bromine, iodine, alkoxy, amino, cyano, nitro, C1-C4-alkyl or is unsubstituted phenyl or phenyl substituted by s radicals selected from the group consisting of chlorine, fluorine, methoxy and ethoxy,
- R2 is C1-C4-alkyl or is unsubstituted phenyl or phenyl substituted by s radicals selected from the group consisting of chlorine, fluorine, methoxy and ethoxy,
- s is 1, 2 or 3.
1 more element
Dependencies are inferred from the claim text.