In 2015,Chen, Zhilong; Wang, Qiu published 《Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones》.Organic Letters published the findings.Reference of Methyl 4-fluoro-3-nitrobenzoate The information in the text is summarized as follows:
A novel approach toward the synthesis of sterically hindered o-aminophenols has been achieved by a formal aryne insertion into hydroxyindolinones. This transformation offers a rapid and efficient entry to diverse o-aminophenol scaffolds under mild transition-metal-free conditions. The reaction involves the addition of hydroxyindolinones to arynes followed by a chemo- and regioselective [1,3]-rearrangement. E.g., in presence of KF and 18-crown-6-, reaction of 1-hydroxy-3,3-dimethylindolin-2-one and o-TMSC6H4OTf gave 60% 1-(2-hHydroxyphenyl)-3,3-dimethylindolin-2-one (I). Furthermore, the reactions of N-hydroxyindoles and arynes were found to provide the C3-aryl indole products via an alternative [3,3]-rearrangement pathway. In the experiment, the researchers used Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9Reference of Methyl 4-fluoro-3-nitrobenzoate)
Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9) belongs to methyl benzoate. Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.Reference of Methyl 4-fluoro-3-nitrobenzoateMethyl 4-fluoro-3-nitrobenzoate is used to prepare dimethyl 3-nitro-3′,4-oxydibenzoate by reacting with 3-hydroxy-benzoic acid methyl ester.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics