4,5-Dibromo-2H-1,2,3-triazole
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4,5-Dibromo-2H-1,2,3-triazole
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CAS No:
22300-52-3
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Formula:
C2HBr2N3
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Chemical Name:
4,5-Dibromo-2H-1,2,3-triazole
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Synonyms:
4,5-dibromo-1,2,3-triazole;4,5-Dibromo-1H-1,2,3-triazole;4,5-Dibromo-2H-1,2,3-triazole;22300-52-3;1H-1,2,3-Triazole, 4,5-dibromo-;C2HBr2N3;4,5-dibromo-2H-triazole;dibromotriazole;dibromo triazole
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CAS No:
4,5-Dibromo-2H-1,2,3-triazole Use and Manufacturing
Into a 3000-mL 3-necked round-bottom flask, was placed 2H-1, 2, 3-triazole (100 g, 1.45 mol, 1.00 equiv), water (1000 mL), Br4, 5-dibromo-2H-l, 2, 3-triazole. Bromine (15 mL) was added dropwise to a stirred solution of 2H-l, 2, 3-triazole (15.0 g, 217 mmol) in water (200 mL) at 0°C. Once addition was completed, the mixture was stirred for 12 hours at room temperature. The resultant mixture was filtered off and washed with water, dried over sodium sulfate and recrystallized from methanol to afford 4, 5-dibromo-2H-l, 2, 3-triazole as a dark brown solid (29.8 g, 60.8percent).[0260] Bromine (11.59 g, 73.35 mmol) was added dropwise to a 0 °C solution of 2H-l, 2, 3-triazole (5.00 g, 72.46 mmol) in water (50 mL), and the resulting solution was allowed to warm to room temperature and stir overnight. The precipitate was collected by filtration and dried to afford 4, 5- dibromo-2H-l , 2, 3-triazole (8.00 g, 49percent) as a white solid. MS (ESI, pos. ion) m/z 228, 226, 230 [M+H]The reactionmixture of To a solution ofTo a 20-L round- bottom flask were placed 4- Fluoro-3-nitroanisole (3.44 g, 1 eq.), 4, 5-dibromo-2/-/-1 , 2, 3-triazole (4.56 g, 1 eq.)1, K2C03 (2.78 g, 1 eq.) and DMF (30 mL) are heated to 1 10 C for 32 h. The reaction mixture is cooled to 22 C and treated with water (70 mL). The resulting suspension is filtered, washed with water (15 mL). The product is slurried in isopropanol (40 mL), filtered and dried under reduced pressure to yield a white solid. Yield: 6.42 g, 84%. Purity: 100% a/a (LC-MS method 2). 1H NMR (400 MHz, CDCI3) delta: 7.71 (d, J = 8.9 Hz, 1 H), 7.47 (d, J = 2.8 Hz, 1 H), 7.25 (dd, Ji = 2.8 Hz, J2 = 8.9 Hz, 1 H), 3.97 (s, 3 H).
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