Method for preparing para-phenyl alkynyl benzaldehydes
AssigneeLaboratoires Serono SA
InventorsDominique Swinnen, Danig Pohin
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Abstract
The present invention is related to a new synthesis for preparing para-phenyl alkynyl benzaldehyde of general formula (I). The compounds of formula (I) are useful building blocks, in particular in the synthesis of electrically conducting polymers. R is selected from the group consisting of C1-C12-alkyl, C1-C12-alkyl aryl, C1-C12-alkyl heteroaryl, C2-C12-alkenyl, C2C12-alkenyl aryl, C2-C12-alkenyl heteroaryl, C2-C12-alkynyl, C2-C12-alkynyl aryl, C2-C12-alkynyl heteroaryl, C3-C8-cycloalkylC1-C12-alkyl-C3-C8-cycloalkyl, C1-C12-alkoxy, aryl, heteroaryl, halides.
Claims14
A process for the preparation of compounds of formula (I):
- wherein R is C1-C12-alkyl, C1-C12-alkyl aryl, C1-C12-alkyl heteroaryl, C2-C12-alkenyl, C2-C12-alkenyl aryl, C2-C12-alkenyl heteroaryl, C2-C12-alkynyl, C2-C12-alkynyl aryl, C2-C12-alkynyl heteroaryl, C1-C12-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl, C1-C12-alkoxy, aryl, heteroaryl, or a halide;
- said process comprising the steps of:
- Step 1:
- reacting an acyl chloride of formula (III) with an alkyl benzene of formula (IV) to yield the corresponding compound (V):
- wherein LG is a leaving group;
- Step 2:
- transforming a compound of formula (V) into compound of formula (VI), using a suitable halogenating agent:
- Step 3:
- subjecting a compound (VI) to an elimination reaction to provide a compound of formula (VII):
- Step 4:
- subjecting a compound of formula (VII) or an activated species thereof with a formylating agent (VIII) for giving the compound (I):
Dependencies are inferred from the claim text.