4-Chloro-3-nitrobenzoic acid → 4-Chloro-3-nitrobenzoyl chloride

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Reaction Steps

As shown in scheme D, reaction of 4-chloro-3-nitrobenzoic acid with thionyl chloride gave 4-chloro-3-nitrobenzoyl chloride, which on further treatment with benzyl glycinate in presence of triethylamine gave benzyl 2-(4-chloro-3-nitrobenzamido)acetate (intermediate 5). The intermediate 5 is treated either with K18F or K19F in the presence of kryptofix[2.2.2] or 18-crown-6 to yield benzyl 2-(4-fluoro-3-nitrobenzamido)acetate, which on further reduction with hydrogen gas or hydrogen source in the presence of Pd/C gave compound 3.

Provenance & Evidence