Hydrochloric Acid → 2-Chloro-5-[(2,2,2-trifluoroethylamino)sulfonyl]-4-fluorobenzoic acid

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Reaction Steps

4.997 g (18.3 mmol) 3-chlorosulfonyl-4-fluorobenzoic acid, 2.90 g (27.5 mmol) NaHCO3 were dissolved in 50 mL water. 1.45 mL (18.3 mmol) trifluoroethylamine was added dropwise to solution. Solution was acidified to pH=1 with concentrated HCl and product was extracted into ethyl acetate. Dried over MgSO4 and concentrated. 5.27 g recovered (83% yield). Crude product was used in subsequent step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 9.22-9.37 (dt, 1H, J=6.44, 30.24 Hz), 7.80-7.92 (dd, 1H, J=9.91, 25.78 Hz), 4.04-4.16 (m, 1H), 3.77-3.90 (m, 1H).

Provenance & Evidence