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US 2010/0076229 A1Published application
Method for Producing Alkenylnitrobenzene Derivatives Unbranched in the 1'-Position
AssigneeBayer CropScience AG
InventorsAlexander Straub, Jorg Nico Greul, Norbert Lui
Life of this patent
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Abstract
The present invention relates to a process for preparing alkenylnitrobenzenes and alkylanilines, which are of significance as intermediates for fungicidally active alkylanilides.
Claims8
An alkenylnitrobenzene of the formula (I)
- where
- R1 is halogen, or —CR′(CF3)2 and R′ is selected from the group consisting of H, F and O—C1-4-alkyl and
- R2 is t-butyl or cyclopropyl.
A hydroxyalkylnitrobenzene of the formula (IV)
- where
- R1 is hydrogen, halogen, or —CR′(CF3)2 and R′ is selected from the group consisting of H, F and O—C1-4-alkyl and
- R2 is cyclopropyl or t-butyl.
An alkylnitrobenzene of the formula (VI)
- where
- R1 is halogen, or —CR′(CF3)2 and R′ is selected from the group consisting of H, F and O—C1-4-alkyl.
A compound of the formula (V)
- where
- R1 is hydrogen, halogen, or —CR′(CF3)2 and R′ is selected from the group consisting of H, F and O—C1-4-alkyl,
- X is a halogen atom or a leaving group and
- R2 is cyclopropyl or t-butyl.
1 more element
A process for preparing an alkenylnitrobenzene of the formula (I)
- where
- R1 is hydrogen, halogen, or —CR′(CF3)2 and R′ is selected from the group consisting of H, F and O—C1-4-alkyl and
- R2 is cyclopropyl or t-butyl,
- comprising the steps of
- reacting a 2-nitrotoluene of the formula (II)
- with an aldehyde aldehydes of the formula (III),
- R2—CHO (III)
- in the presence of a base to give a hydroxyalkylnitrobenzene of the formula (IV)
- in which
- R1 and R2 are as defined above;
- (ii) converting the hydroxyalkylnitrobenzene of the formula (IV) obtained from step (i)
- to a compound of the formula (V)
- in which R1 and R2 are each as defined above, and X is a halogen atom or a leaving group;
- and
- (iii) eliminating HX from the compound of the formula (V) to give an alkenylnitrobenzene of the formula (I),
- or
- (iv) directly eliminating H2O from the hydroxyalkylnitrobenzene of the formula (IV) to give an alkenylnitrobenzene of the formula (I).
14 more elements
(canceled)
Dependencies are inferred from the claim text.