Trimethyl orthoacetate → Methyl 4-iodo-3-nitrobenzoate

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Reaction Steps

We have also found an alternative, more efficient and simple method for esterification using trimethyl orthoacetate. The method involves dissolving 4-iodo-3-nitrobenzoic acid in trimethyl orthoacetate and refluxing the solution for 15 hours. Removal of the solvent under reduced pressure, gives 4-iodo-3-nitro benzoic methyl ester as a solid in almost quantitative yield (98%, 97% HPLC). It contains about 1.5% starting acid. Since the residual starting acid does not interfere in the next step, the material can be taken directly for the next stage. However, if required, the material can be further purified by crystallization from methanol and water with little loss of yield (95% Y, 98.3% HPLC).

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