反应详情

温度

80 °C

To a solution of 4-fluoro-1-nitrobenzene (12.5 g, 89 mmol) and 1H-tetrazole (6.21 g, 89 mmol) in DMF (89 mL) stirred at room temperature, potassium carbonate (12.24 g, 89 mmol) was added in one portion. The resulting mixture was stirred at 80° C. overnight, and then reaction mixture was worked up by the addition of water at 80° C., then cooled to room temperature, and stirred at room temperature for 30 minutes. The yellow solid was collected by filtration, washed with water, air-dried for 2 hours, and dried in an vacuum oven at 60° C. for 2 hours to afford a mixture of 4-(1H-tetrazol-1-yl)-1-nitrobenzene and 4-(2H-tetrazol-2-yl)-1-nitrobenzene. The product thus obtained was re-dissolved in THF (209 mL) and, while stirring at room temperature, platinum(IV) oxide (0.45 g, 1.982 mmol) was added in one portion. The resulting mixture was stirred at room temperature overnight under a hydrogen atmosphere, after which the reaction mixture was worked up by filtration through a celite pad and the solvent removed by evaporation. The residue was purified and separated by CombiFlash® (0-50% EtOAc/toluene; Teledyne Isco, Inc., Lincoln, Nebr.) to afford the desired 4-(2H-tetrazol-2-yl)aniline as a yellowish solid. 1H NMR (400 MHz, DMSO-d6): δ 9.08 (s, 1H), 7.72 (d, 2H), 6.73 (d, 2H), 5.75 (s, 2H).

1. customreaction mixture
2. temperaturecooled to room temperature
3. stirringstirred at room temperature for 30 minutes
4. filtrationThe yellow solid was collected by filtration
5. washwashed with water
6. customair-dried for 2 hours
7. customdried in an vacuum oven at 60° C. for 2 hours
8. customto afford
9. customThe product thus obtained
10. stirringwhile stirring at room temperature
11. stirringThe resulting mixture was stirred at room temperature overnight under a hydrogen atmosphere
12. filtrationafter which the reaction mixture was worked up by filtration through a celite pad
13. customthe solvent removed by evaporation
14. customThe residue was purified
15. customseparated by CombiFlash® (0-50% EtOAc/toluene; Teledyne Isco, Inc., Lincoln, Nebr.)