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 - 3
H-isobenzofuran-1-ones - directed
ortho-lithiation - ring-chain tautomers
