1,3-Dibromopropane → 4-(3-Bromopropoxy)-2-nitroaniline

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 and was complete in 6 hours. The reaction mixture was cooled to room temperature, filtered and washed with excess acetone. The organic layer was removed on a rotary evaporator under reduced pressure and the resulting brown gelatin was purified by silica column chromatography using 40% hexane in dichloromethane as eluent. 20.0 g of 4-(3-bromopropoxy)-2-nitroaniline was obtained as a dark orange liquid which was used without any further purification. MS (EI: 276 (MH+).

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