Ammonia → 2,3,4,5-Tetrafluoro-6-nitroaniline

HRID 53722Notes

Reaction equation

HRID 53722 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

4

Reactant 2

HCID 222AmmoniaHCID 70154Pentafluoronitrobenzene

Product 1

HCID 27757602,3,4,5-Tetrafluoro-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 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).

Workup

  1. customformed
  2. customThe precipitate (ammonium fluoride) was separated by vacuum filtration
  3. washwashed with ether (30 mL)
  4. customThe filtrate was rotary evaporated
  5. customthe resulting orange crystals gave 3 spots on TLC (alumina, benzene)
  6. customPurification of this sample
  7. customPurification of this sample
  8. customThe first band was collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-63b14e78690249429d9e321bec6cc11a
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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