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US 6,855,842 B1Granted
Intermediates for making a bezofuran or benzothiophene derivative nitrated in position 5 and uses thereof
AssigneeRhodia Chimie
InventorsThierry Schlama, Armand Mettling, Philippe Karrer
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Abstract
The invention concerns novel nitroaromatic compounds of general formula (I′) wherein: R, R′1, R2, Z and n are as defined in claim 1. The invention also concerns a method for preparing nitroaromatic compounds nitrated in position 4. The invention further concerns the use of said compounds for preparing heterocyclic benzofuran or benzothiophene derivatives nitrated in position 5. The invention concerns particularly the preparation of 2-alkyl-5-nitrobezofuran.
Claims24
A process for preparing nitroaromatic compounds with formula(I):
- wherein:
- R1 represents a linear or branched alkyl group containing 1 to 12 carbon atoms, a phenyl group optionally substituted by an allyl group containing 1 to 4 carbon atoms, or a halogenophenyl group;
- R2 represents a hydrogen atom, or a hydrocarbon group containing 1 to 12 carbon atoms, being a linear or branched alkyl group, a cycloalkyl group, a phenyl group or a phenylalkyl group;
- Z represents an oxygen or sulfur atom;
- R represents a hydrogen atom or a group selected form the group consisting of:
- a hydroxyl group;
- a linear group containing 1 to 6 carbon atoms;
- an alkoxy group containing 1 to 6 carbon atoms;
- an ester group containing 1 to 10 carbon atoms;
- an alkylamide group containing 1 to 6 carbon atoms;
- a carboxamide group;
- a halogen atom;
- and
- a trifluoromethyl group;
- and
- n is a number equal to 1, 2 or 3;
- said process comprising the step of carrying out a selective nitration in position 4 of a stating aromatic compound, using a source of NO2+, in the presence of sulfuric acid, the starting aromatic compound having the following formula (II):
- wherein R, R1 , R2, Z and n have the meanings given above.
15 more elements
A nitroaromatic compound with the following formula (I′):
- wherein
- R represents a hydrogen atom or a group selected form the group consisting of the following group;
- a hydroxyl group;
- a linear or branched alkyl group containing 1 to 6 carbon atoms;
- an alkoxy group containing 1 to 6 carbon atoms;
- an ester group containing 1 to 10 carbon atoms;
- an alkylamide group containing 1 to 6 carbon atoms;
- a carboxamide group;
- a halogen atom;
- and
- a trifluoromethyl group
- R′1 represents a linear or branched alkyl group containing 1 to 12 carbon atoms, a phenyl group optionally substituted by an alkyl group containing 1 to 4 carbon atoms, or a halogenophenyl group;
- R2 represents a hydrogen atom, or a hydrocarbon group containing 1 to 12 carbon atoms, being a linear or branched alkyl group, a cycloalkyl group, a phenyl group or a phenylalkyl group;
- Z represents an oxygen or sulphur atom;
- R represents a hydrogen atom or a substituent;
- and
- n is a number equal to 1, 2 or 3.
14 more elements
Dependencies are inferred from the claim text.