4-Fluorobenzenesulfonyl chloride → N-(3,4-dimethoxyphenyl)-4-fluorobenzenesulfonamide

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Reaction Steps

3,4-Dimethoxyaniline(1.01 g, 6.99 mM) was added to a solution of 4-Fluorobenzenesulfonyl chloride (1.50 g, 7.69 mM) in anhydrous pyridine(10 ml). The reaction was stirred overnight. The reaction was quenched with 1N HClaq.(20 ml) and washed with ethyl acetate(3×20 ml). The organic extracts were combined, dried(sodium sulfate), solids filtered off and concentrated. The desired product was isolated using silica gel flash chromatography of 1.30 g as a yellow solid. H1 NMR(CDCl3) δ 3.79(s, 3H), 3.86(s, 3H), 6.50(d, 1H, J=4.71 Hz), 6.68(d, 1H, J=2.64 Hz), 6.71(d, 1H, J=2.76 Hz), 7.11(d, 2H, J=8.67 Hz), 7.75(m, 2H). MS(ES) m/z 328.9; (M+NH4+); HRMS for (MH+) C14H14SFNO4: 260.1511.

Provenance & Evidence