Functionalization of 3-Chlorobenzaldehyde

Synthesis 2012
Kristīne Aksjonova, Sergejs Beļakovs, Edvards Liepiņš, A. Boman, T. Lundstedt, P. Lek, P. Trapencieris

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.

Keywords
3-chlorobenzaldehyde - 2,3-dihydroisoindol-1-ones - 3H-isobenzofuran-1-ones - directed ortho-lithiation - ring-chain tautomers
DOI
10.1055/s-0031-1289784

Aksjonova, K., Beļakovs, S., Liepiņš, E., Boman, A., Lundstedt, T., Lek, P., Trapencieris, P. Functionalization of 3-Chlorobenzaldehyde. Synthesis, 2012, Vol.44, No.14, pp.2200-2208. ISSN 0936-5214. Available from: doi:10.1055/s-0031-1289784

Publication language
English (en)