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Synthesis 2012; 44(14): 2200-2208
DOI: 10.1055/s-0031-1289784
DOI: 10.1055/s-0031-1289784
paper
Functionalization of 3-Chlorobenzaldehyde
Further Information
Publication History
Received: 30 January 2012
Accepted after revision: 11 May 2012
Publication Date:
19 June 2012 (online)
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Abstract
2-Substituted 3-chlorobenzaldehydes were prepared from the corresponding 2-(3-chlorophenyl)-1,3-dioxolanes using an ortho-lithiation strategy. The 6-chloro-2-formylbenzamide exists only in a ring form, but 6-chloro-2-formylbenzoic acid esters were isolated in both forms as open chain and cyclic tautomers. 7-Chloro-3-hydroxy-3H-isobenzofuran-1-one reacted with nucleophilic reagents at the carbonyl or quaternary carbon depending on the character of nucleophile.
Key words
3-chlorobenzaldehyde - 2,3-dihydroisoindol-1-ones - 3H-isobenzofuran-1-ones - directed ortho-lithiation - ring-chain tautomersSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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Reviews on ortho-lithiation: