Reacción #82000

Ecuación de reacción

Ammonia

pentafluoronitrobenzene

→

2-Nitro-3,4,5,6-tetrafluoroaniline

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroformed
2. 2
   OtroThe precipitate (ammonium fluoride) was separated by vacuum filtration
3. 3
   Lavadowashed with ether (30 mL)
4. 4
   OtroThe filtrate was rotary evaporated
5. 5
   Otrothe resulting orange crystals gave 3 spots on TLC (alumina, benzene)
6. 6
   OtroPurification of this sample
7. 7
   OtroPurification of this sample
8. 8
   OtroThe first band was collected
9. 9
   Concentraciónconcentrated

Procedimiento

2-Nitro-3,4,5,6-tetrafluoroaniline was prepared using an adaptation of the method of Brooke et al., J. Chem. Soc. 802 (1961). Ammonia gas was bubbled through a solution of pentafluoronitrobenzene (3.00 g, 114.1 mmol) in 200 mL anhydrous diethyl ether for 4 h. During this time the color changed from clear white to a deep yellow and a white precipitate formed. The precipitate (ammonium fluoride) was separated by vacuum filtration and washed with ether (30 mL). The filtrate was rotary evaporated and the resulting orange crystals gave 3 spots on TLC (alumina, benzene). Purification of this sample was achieved by column chromatography (basic alumina, benzene). Purification of this sample was achieved by column chromatography (basic alumina, activity II) on a 1.5"×20" column. The first band was collected and concentrated to yield a yellow solid 1.88 g (63.0%), mp 44.5-45 (lit. 42.5°-43.5° C.). 19F NMR (C6F6 external standard, δ -162.9) δ -149.9(m), -1.56.6(m), -162.0 (m), -178.3(m).

Fuente