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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 6
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Original Articles

Ortholithiation of Unprotected Benzoic Acids: Application for Novel 2‐Chloro‐6‐Substituted Benzoic Acid Syntheses

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Pages 799-806 | Published online: 20 Aug 2006
 

Abstract

2‐Chloro‐6‐substituted benzoic acids of the type 2a–h were prepared by the tandem metallation sequence from 2‐chlorobenzoic acid 1 with the 1:1 complex sec‐butyllithium/TMEDA in THF at −78°C followed by quenching with electrophiles.

Acknowledgment

This research was supported by the CNRS, Université du Maine, and Institut universitaire de France.

Notes

12‐Chlorobenzoic acid (1) is very cheap (€ 30/kg).

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