Ethyl Bromide → Ace-011

Participants

Reaction Conditions

Reaction Steps

A 12-L, 4-necked flask equipped with a reflux condenser, nitrogen inlet, thermocouple, addition funnel, and mechanical stirrer was charged with 400 g 2-Acetamido-5-nitrophenol. The flask was charged with 790 g potassium carbonate and 2.0 L of dimethylformamide (DMF). The mixture was stirred and warmed to 60±2.50° C. 294 g of ethyl bromide or ethyl iodide was added over 10 minutes to one hour while maintaining a 60° C. internal temperature. The reaction mixture was stirred for at least one hour or until the mixture turned yellow and the concentration of 2-Acetamido-5-nitrophenol was less than 1%, if needed additional ethyl bromide or ethyl iodide was added to reduce the concentration of 2-Acetamido-5-nitrophenol present. The mixture was cooled to 20±5° C. 4 L of water was added and while maintaining a 25±5° C. internal temperature. The suspension was stirred for a minimum of 30 minutes and collected by vacuum filtration. The product was washed and the pH monitored for a pH of <8. If the pH was >8, the product was washed with 1.0 L portions of warm water until the pH was <8. The resultant product was washed with heptane and vacuum dried. Yield 98%, strength 98.6%, mp 164-165° C.

Provenance & Evidence