Hydrogen Bromide → Benzonitrile, 4-bromo-

Participants

Reaction Conditions

Reaction Steps

Water (45 ml) and 48% hydrobromic acid (27 ml) were added to 4-aminobenzonitrile (2d) (2.36 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. The mixture was heated to 55° C., then stirred for approximately 2 hours, and cooled to room temperature. Then, a 10 mol/L aqueous sodium hydroxide solution (40 ml) was added thereto, followed by extraction twice with toluene (300 ml). The toluene layers were combined and washed with water (50 ml). The solvent was distilled off by the concentration of the toluene layer under reduced pressure to obtain 4-bromobenzonitrile (1d) (3.35 g, 83.0%). The instrumental spectrum data and HPLC retention time (Rt) of the obtained compound (1d) were completely consistent with those of the commercially available compound (1d).

Provenance & Evidence