1,3-Dibromopropane → 2-(4-Amino-3-nitrophenoxy)ethyl bromide

Participants

Reaction Steps

A 500 mL flask was charged with 4-amino-3-nitrophenol (15.4 g, 100 mmol, commercially available from Aldrich). Acetone (300 mL), cesium carbonate (39.09 g, 120 mmol) and 1,3-dibromopropane (40.84 mL, 400 mmol) were added to the flask and stirred at refluxed temperature. The reaction was monitored by LCMS. After 6 hours, the reaction mixture was cooled to room temperature, filtered and washed with acetone. The organic layer was removed on a rotary evaporator under reduced pressure and the resulting material was purified by silica column chromatography using 40% hexane in dichloromethane as eluant. 20 g of 4-(2-bromoethoxy)-2-nitroaniline was isolated which was used in the next step without any further purification. MS (EI): 275 (MH+).

Provenance & Evidence