Ammonium Chloride → 1-(3-Amino-5-bromo-2-hydroxyphenyl)ethanone

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Reaction Steps

A mixture of 1-(5-bromo-2-hydroxy-3-nitrophenyl)ethanone (25 g, 96 mmol), iron (27 g, 481 mmol), and NH4Cl (5.1 g, 96 mmol) in EtOH/H2O (5:1,300 ml) was heated at reflux in 2 h, the mixture was cooled filtered the solid, the filtrate was concentrated, taken up in H2O, extracted with DCM (3×), dried over MgSO4, concentrated and purified by ISCO (10% EtOAc/Hexanes) to give the title compound as a yellow solid. MS (m+2): 232.1.

Provenance & Evidence