2,3-Dichloropyridines undergo a mono- or a dicarbonylation in the presence of carbon monoxide, an alc., and a palladium catalyst, affording selectively either alkyl 3-chloropyridine-2-carboxylates or dialkyl pyridine-2,3-dicarboxylates in good yields, depending on the reaction conditions. For instance, the process could be scaled up for the monoalkoxycarbonylation of 2,3-dichloro-5-(trifluoromethyl)pyridine, affording in high yield and selectivity the corresponding 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylate. [on SciFinder (R)]
Title
Synthetic process development and scale up of palladium-catalyzed alkoxycarbonylation of chloropyridines
Published in
Organic Process Research & Development
Volume
5
Issue
6
Pages
572-574
Date
2001
ISSN
1083-6160
Note
CAN 136:167264
27-16
Heterocyclic Compounds (One Hetero Atom)
Department of Process Research,LONZA Ltd.,Visp,Switz.
Journal
written in English.
3375-31-3; 12150-46-8 (1,1'-Bis(diphenylphosphino)ferrocene) Role: CAT (Catalyst use), USES (Uses) (process for large-scale regioselective palladium-catalyzed alkoxycarbonylation of chloropyridines); 128073-16-5P Role: IMF (Industrial manufacture), SPN (Synthetic preparation), PREP (Preparation) (process for large-scale regioselective palladium-catalyzed alkoxycarbonylation of chloropyridines); 52334-81-3 (2-Chloro-5-trifluoromethylpyridine); 69045-84-7 (2,3-Dichloro-5-trifluoromethylpyridine) Role: RCT (Reactant), RACT (Reactant or reagent) (process for large-scale regioselective palladium-catalyzed alkoxycarbonylation of chloropyridines); 120083-60-5P; 128072-94-6P Role: SPN (Synthetic preparation), PREP (Preparation) (process for large-scale regioselective palladium-catalyzed alkoxycarbonylation of chloropyridines)
Record creation date
2007-12-17
