Acetyl bromide → HCID 22317679, compound

Participants

Reaction Steps

2-Ethyl-6-methyl-4-nitropyridine N-oxide (36.4 g) was added to 60 g of acetic acid and the mixture was warmed to give a clear solution which was cooled to 15°-20° C. and treated dropwise, keeping the temperature below 25° C., with 49.2 g of acetyl bromide. After addition was complete, the mixture was stirred at room temperature for 11/2 hours and then slowly warmed to 65°-70° C. and kept in this temperature range for 24 hours. The acetic acid and volatile components were removed in vacuo and 200 ml of chloroform were added to the residue. To the chilled mixture there was added dropwise 58 g of phosphorus tribromide at 10° C. and the mixture was warmed to room temperature and then heated at reflux for 3 hours. An additional 10 g of phosphorus tribromide were added and the mixture was heated for 1 hour, poured onto ice, neutralized with cold 35% sodium hydroxide and extracted three times with 200 ml of methylene chloride. The organic extract was concentrated, 300 ml of diethyl ether were added and the ether solution was dried over magnesium sulfate and concentrated. The crude product was fractionated in vacuo to give 30 g of the title product as a yellow oil; bp13 120°-130° C.

Provenance & Evidence