Synthesis 2012; 44(14): 2200-2208
DOI: 10.1055/s-0031-1289784
paper
© Georg Thieme Verlag Stuttgart · New York

Functionalization of 3-Chlorobenzaldehyde

Kristine Aksjonova
a   Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia
,
Sergey Belyakov
a   Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia
,
Edvards Liepinsh
a   Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia
,
Arne Boman
b   AcurePharma AB, Ulleråkersvägen 38, 75643 Uppsala, Sweden, Email: peteris@osi.lv
,
Torbjorn Lundstedt
b   AcurePharma AB, Ulleråkersvägen 38, 75643 Uppsala, Sweden, Email: peteris@osi.lv
,
Per Lek
b   AcurePharma AB, Ulleråkersvägen 38, 75643 Uppsala, Sweden, Email: peteris@osi.lv
,
Peteris Trapencieris*
a   Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia
› Author Affiliations
Further Information

Publication History

Received: 30 January 2012

Accepted after revision: 11 May 2012

Publication Date:
19 June 2012 (online)


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.

Supporting Information

 
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