The reaction of diazomethane with 3-carboxy-4-fluorophenyltrimethylammonium iodide (1) affords, not the methyl ester, but the betaine 2-fluoro-5-trimethylammoniobenzoate (2). However, when the iodide anion is replaced by a weaker nucleophile, tetrafluoroborate, the methyl ester is obtained. A mechanism for the betaine reaction is outlined.
S. E. Drewes, H. E. M. Magojo and D. A. Sutton, J. Chem. Soc., Perkin Trans. 1, 1975, 1283 DOI: 10.1039/P19750001283
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