Hydrogen Bromide → Benzene, 1-bromo-3-nitro-

Participants

Reaction Conditions

Reaction Steps

Water (45 ml), acetonitrile (6 ml), and 48% hydrobromic acid (27 ml) were added to 3-nitroaniline (2c) (2.76 g, 20 mmol) at room temperature. To the mixed solution, 2,2,6,6-tetramethylpiperidine 1-oxyl (0.31 g, 2 mmol) was added at room temperature, and the mixture was cooled to 10° C. or lower. Then, sodium nitrite (2.07 g) dissolved in water (15 ml) was added thereto. After stirring at room temperature for approximately 2 hours, a 10 mol/L aqueous sodium hydroxide solution (30 ml) was added thereto, and the precipitated crystals were collected by filtration, washed with water (40 ml), and then dried under reduced pressure to obtain 3-bromonitrobenzene (1c) (3.75 g, 93.0%). The instrumental spectrum data and HPLC retention time (Rt) of the obtained compound (1c) were completely consistent with those of the commercially available compound (1c).

Provenance & Evidence