Sulfuric Acid → 2-Azido-1,3,5-tribromobenzene

Participants

Reaction Conditions

Reaction Steps

2,4,6-Tribromoaniline (34.16 g, 103.6 mmol) was mixed with acetic acid (600 mL) and sulfuric acid (130 mL) at room temperature. The mixture was stirred to obtain a solution and then cooled in an ice bath to an internal temperature of 10° C. A solution of NaNO2 (7.65 g, 111 mmol) in water (22 mL) was added dropwise over 30 minutes while maintaining the internal temperature of the reaction mixture below 12° C. The reaction mixture was allowed to stir for 30 minutes at the same temperature. A solution of urea (0.90 g) in water (2 mL) was added and the mixture stirred for an additional 10 minutes. A solution of NaN3 (7.65 g, 118 mmol) in water (22 mL) was slowly added and the mixture stirred for an additional 1 hour. Cold water (900 mL) was then slowly added in portions and the mixture stirred for 30 minutes. The precipitate was filtered, washed with water, dissolved in diethyl ether, dried over sodium sulfate and concentrated to give the subtitle compound as an off-white solid (34.2 g, 93%).

Provenance & Evidence