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

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.

Keywords:

• Alkyllithiums
• benzoic acids
• ortholithiation/substitution

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).