The Journal of Organic Chemistry

Nitro displacement by methanethiol anion. Synthesis of bis-, tris-, tetrakis-, and pentakis (methylthio) benzoic acids and related derivatives

JR Beck, JA Yahner

Index: Beck,J.R.; Yahner,J.A. Journal of Organic Chemistry, 1978 , vol. 43, # 10 p. 2052 - 2055

Full Text: HTML

Citation Number: 8

Abstract

Results Three general procedures were used for the synthesis of the benzoic acids.'The first (Scheme I) involved treatment of 4-chloro-3, 5-dinitrobenzoic acid (1) with excess methanethiol anion (lithiuE salt) in cold DMF for 0.5 h to yield 3, 4-bis (methylthio)-5- nitrobenzoic acid (2, 80%). Attempted displacement of the second nitro group at elevated temperature and longer reaction time was unsuccessful. The benzoic acid 2 was ...