Cesium carbonate → HCID 57585897, compound

Participants

Reaction Steps

4-amino-3-nitrophenol (25 g, 162 mmol), 4-fluorobenzaldehyde (19.1 g, 154 mmol) and cesium carbonate (58 g, 178 mmol) were stirred in dimethylformamide at 85 degrees centigrade for 20 minutes and then 45 degrees Centigrade for approximately 18 hours. The reaction was allowed to cool to room temperature then filtered through celite and eluted with ethyl acetate. Water, brine and ethyl acetate were added to the filtrate which was then filtered through a glass wool packed Alltech 75 mL Extract-Clean™ filter column. The filtrate was separated into two portions and each was extracted with ethyl acetate then washed with brine four times. The organic layers were combined, dried over magnesium sulfate, concentrated onto basic alumina and purified by silica gel column chromatography (0 to 100% ethyl acetate in hexanes to give 23 g of 4-[(4-amino-3-nitrophenyl)oxy]benzaldehyde. (M+1) 259.0, 2.39 min (LC/MS method A)

Provenance & Evidence