Ethanolamine → 2-((2-Chloro-3-fluoro-6-nitrophenyl)amino)ethan-1-ol

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Reaction Steps

2-Chloro-1,3-difluoro-4-nitrobenzene (5.37 g, 27.7 mmol), ethanolamine (1.69 g, 27.7 mmol) and Et3N (2.80 g, 27.7 mmol) are stirred in EtOH (40.0 mL) at room temperature for 2 hours. The solvent is then evaporated, and the resulting residue is suspended in EtOAc (50.0 mL) and washed with 0.5 N NaOH (50.0 mL). The aqueous phase is extracted 4 times with EtOAc (4×50.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated. The product is purified by flash chromatography on silica gel, eluting with mixtures of heptane and EtOAc (5.53 g, 85%). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.39 (dd, J=10.55, 5.27 Hz, 2H) 3.53 (t, J=5.47 Hz, 2H) 4.89 (s, 1H) 6.89 (dd, J=9.37, 8.01 Hz, 1H) 7.19 (t, J=4.69 Hz, 1H) 8.01 (dd, J=9.47, 5.96 Hz, 1H).

Provenance & Evidence