Hydrogen Bromide → 5-Bromo-2-chloronitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-3-nitro-phenylamine (17.2 g, 0.1 mol) in 260 mL HBr (48%) at 0° C. was added dropwise NaNO2 (13.8 g, 0.2 mol) in water. The reaction mixture was stirred for 1 h at 0° C. then CuBr (24 g, 0.17 mol) was added in portions to the mixture and stirred for an additional 1 h. Water was added, the mixture allowed to warm to room temperature and was then extracted with EtOAc. The crude product was purified by silica gel column chromatography to give the title compound (13 g, 55%).

Provenance & Evidence