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

Temperature

10 °C

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%).

1. customto obtain a solution
2. temperaturewhile maintaining the internal temperature of the reaction mixture below 12° C
3. stirringto stir for 30 minutes at the same temperature
4. stirringthe mixture stirred for an additional 10 minutes
5. stirringthe mixture stirred for an additional 1 hour
6. stirringthe mixture stirred for 30 minutes
7. filtrationThe precipitate was filtered
8. washwashed with water
9. dissolutiondissolved in diethyl ether
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated

ORD record

ord-a83ff061d01c400f8c94fc97f7651de5

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772235B2