Trifluoroacetic acid → 3-Fluoro-2-nitroaniline

HRID 1922756Notes

Reaction equation

HRID 1922756 reaction equation
[F:1][C:2]1[C:3]([N+:28]([O-:30])=[O:29])=[C:4]([N:8]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>O>[F:1][C:2]1[C:3]([N+:28]([O-:30])=[O:29])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605503Benzenamine, 3-fluoro-2-nitro-N-(triphenylphosphoranylidene)-

Product 1

HCID 27828343-Fluoro-2-nitroanilineYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2-5 mL microwave vial equipped with a magnetic follower was charged with 3-fluoro-2-nitro-N-(triphenylphosphoranylidene)benzenamine (585 mg, 1.4 mmol), water (3 mL) and TFA (0.1 mL). The reaction mixture was irradiated at 160° C. for 15 min and then partitioned between water and EtOAc. The organic layer was separated and washed with an saturated aqueous solution of sodium bicarbonate and brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to flash chromatography (Si—PCC, 0-100% Et2O in pentane) to give 3-Fluoro-2-nitrophenylamine as an orange solid (218 mg, 100%). 1H NMR (CDCl3, 400 MHz): δ 7.22 (ddd, J=8.2, 8.2, 5.5 Hz, 1 H); 6.57 (ddd, J=8.5, 1.4, 1.4 Hz, 1 H); 6.48 (ddd, J=11.3, 8.2, 1.4 Hz, 1 H.

Workup

  1. customA 2-5 mL microwave vial equipped with a magnetic follower
  2. customThe reaction mixture was irradiated at 160° C. for 15 min
  3. custompartitioned between water and EtOAc
  4. customThe organic layer was separated
  5. washwashed with an saturated aqueous solution of sodium bicarbonate and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-251f3171515042f59e4c3603062d5519
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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