1-(2-Amino-3-chloro-4-methoxyphenyl)ethanone → 1-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone

Participants

Reaction Conditions

Reaction Steps

1-(2-Amino-4-methoxy-3-chloro-phenyl)ethanone (71.55 g, 358 mmol) was dissolved in HBr (500 mL, 48% in H2O). The reaction was heated to 110° C. for 2 days. The reaction was cooled to rt then the solids were filtered. The solids were partitioned between EtOAc and ½ sat Na2CO3(aq). Organics were dried over Na2SO4, filtered and solvent removed under reduced pressure. 1-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone (15.5 g, 16%) was isolated by silica gel chromatography as an off-white solid.

Provenance & Evidence