2-Bromoaniline → HCID 178471911, compound

Participants

Reaction Steps

To a solution of 2-bromoaniline (2 g, 11.63 mmol) in Isopropanol (15 mL) stirred under nitrogen at room temperature was added neat ethyl 2-(ethoxymethylene)-3-oxobutanoate (2.165 g, 11.63 mmol) in one charge. The reaction mixture was stirred at room temperature for 20 min, at which time LCMS showed only a trace amount of product. The reaction mixture was heated to 75° C. and stirred for 20 min. LCMS showed complete conversion. The mixture was cooled to room temperature and concentrated under vacuum, during which time a large amount of material precipitated out. Filtration followed by a hexanes wash afforded ethyl 2-(((2-bromophenyl)amino)methylene)-3-oxobutanoate (3.8 g, 10.96 mmol, 94% yield) that was apx. 90% pure to be used in the next step. LCMS: (M+H)+: 312.0.

Provenance & Evidence