Diethyl Ether → N-Fluoro-4-methylpyridinium-2-sulfonate

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Reaction Steps

In a reactor, 4-methylpyridine-2-sulfonic acid (3.46 g, 20 mmol) was dissolved in a mixture of acetonitrile (60 ml) and water (6 ml). The reactor was dipped in a cooling bath kept at -20° C., and fluorine gas diluted with nitrogen gas to a concentration of 10% was introduced at a flow rate of 40 ml/min. A total amount of the fluorine gas was 1334 ml (60 mmol). Then, the nitrogen gas alone was introduced at a flow rate of 36 ml/min. for 30 minutes. After the addition of tetrahydrofuran and ethyl ether at -20° C., a crystalline precipitate was recovered by filtration at room temperature. The crystal was washed with ethyl ether and dried under reduced pressure to obtain crystalline N-fluoro-4-methylpyridinium-2-sulfonate (3.04 g, 15.9 mmol). Yield, 80%. A melting point is shown in Table 1. IR and NMR data are as follows:

Provenance & Evidence