3-Bromophenol → HCID 69048156, compound

Participants

Reaction Steps

To a 50 ml of anhydrous N,N-dimethylformamide suspension containing 2.5 g of sodium hydride (55% weight) was added 10.0 g of 3-bromophenol, and the mixture was stirred under ice-cooling for 15 minutes. Subsequently, a solution of 16.6 g of N-(5-chloro-2-nitrophenyl)-N-methylcarbamic acid t-butyl ester dissolved in 70 ml of anhydrous N,N-dimethylformamide was added to the mixture in drops, and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was concentrated, followed by addition of water, neutralization using 3N hydrochloric acid and extraction with ethyl acetate. The extraction solution was washed with saturated saline, and then dried over anhydrous sodium sulfate. Ethyl acetate was distilled off from the extraction solution, and the insoluble product which deposited was washed with hexane and filtered, followed by drying under reduced pressure, to give the title compound (20.2 g, 83% yield).

Provenance & Evidence