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US 8,575,366 B2Granted
Method for producing 2-halogenomethylphenyl acetic acid derivatives
AssigneeBASF SE
InventorsAlexander Korte, Mark Alan Kearns, Jonathan O. Smith, Gunter Lipowsky, Willi Bieche
Life of this patent
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Abstract
The present invention relates to a process for producing 2-halogenomethylphenyl acetic acid derivatives.
Claims10
A process for producing a compound of formula (I)
- wherein X is chlorine or bromine,
- R1 is methyl, ethyl, n-propyl or i-propyl;
- and
- R2 is methyl or ethyl;
- said process comprising providing a compound of formula (II)
- wherein
- R2 is methyl or ethyl;
- and cleaving the compound of formula (II) in the presence of a compound of formula (III)
- R1—OH (III),
- and a halogenating agent selected from the group consisting of thionyl halide, oxalyl halides and mixtures of thionyl bromide and hydrobromic acid, mixtures of thionyl chloride and hydrochloric acid, mixtures of oxalyl chloride and hydrochloric acid or mixtures of oxalyl bromide and hydrobromic acid;
- to obtain a compound of formula (I).
8 more elements
A process for the production of a compound of formula (II),
- wherein R2 is methyl or ethyl, said process comprising reacting a compound of formula (IV)
- with an alkylating agent and a base in an inert organic solvent, wherein the inert organic solvent is toluene;
- to obtain a compound of formula (II).
A process for producing a compound of formula (IV)
- comprising
- a) reacting a compound of formula (V)
- with a nitrosating agent in the presence of an alcohol and a base;
- and
- b) after completion of the reaction adjusting the pH to a pH ≦3.
2 more elements
A process for producing a compound of formula (I)
- wherein R2 is methyl or ethyl;
- and
- X is chlorine or bromine;
- comprising reacting a compound of formula I, wherein R2 is hydrogen with an alkylating agent in an inert organic solvent.
1 more element
A process for producing a compound of formula I, comprising
- a) reacting a compound of formula (V)
- with a nitrosating agent in presence of an alcohol and a base;
- and
- after completion of the reaction adjusting the pH to a pH ≦3;
- reacting the resulting compound of formula (IV)
- with an alkylating agent and a base in an inert organic solvent, wherein the inert organic solvent is toluene to yield a compound of formula (II);
- wherein R2 is methyl or ethyl;
- and cleaving the compound of formula (II) in the presence of a compound of formula (III)
- R1—OH (III),
- or
- b) reacting a compound of formula (V) with a nitrosating agent in the presence of an alcohol and a base;
- and
- after completion of the reaction adjusting the pH to a pH ≦3 to yield a compound of formula (IV);
- cleaving the compound of formula (IV) in the presence of a compound of formula (III)
- R1—OH (III),
- and alkylating the resulting 2-halogenomethylphenyl acetic acid derivatives of formula I
- wherein R2 is hydrogen, and X is chlorine or bromine;
- to the 2-halogenomethylphenyl acetic acid derivatives of formula I, wherein R2 is ethyl or methyl.
15 more elements
Dependencies are inferred from the claim text.