Ammonia → 2,3,4,5-Tetrafluoro-6-nitroaniline
Reaction equation
[NH3:1].[F:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7](F)[C:6]([F:13])=[C:5]([F:14])[C:4]=1[F:15]>C(OCC)C>[N+:9]([C:8]1[C:3]([F:2])=[C:4]([F:15])[C:5]([F:14])=[C:6]([F:13])[C:7]=1[NH2:1])([O-:11])=[O:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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 11) 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).
Workup
- customformed
- customThe precipitate (ammonium fluoride) was separated by vacuum filtration
- washwashed with ether (30 mL)
- customThe filtrate was rotary evaporated
- customthe resulting orange crystals gave 3 spots on TLC (alumina, benzene)
- customPurification of this sample
- customPurification of this sample
- customThe first band was collected
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b32d1719e29c4023b0c90e66a8f3e463
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05622952
Reaction notes
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