3-Fluoro-4-nitrophenol → 4-Amino-3-fluorophenol

HRID 2273933Notes

Reaction equation

HRID 2273933 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[F:11])([O-])=O>C(OCC)(=O)C.C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[F:11]

Participants

5

Reactant 1

HCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 27359194-Amino-3-fluorophenolYield 980%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitro-3-fluorophenol (0.314 g, 2 mmol) and iron (0.56 g, 10 mmol) in ethyl acetate (4 ml) and acetic acid (2 ml) was refluxed for 3 hour. The solid particles were filtered off. The filtrate was washed with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated to yield 4-amino-3-fluorophenol (53a) (0.25 g, 19.6 mmol, 98%) as a brown solid. 1H NMR (CDCl3, 400 MHz) δ 6.48-6.58 (m, 2H), 6.61-6.70 (m, 1H), 7.87 (bs, 3H).

Workup

  1. temperaturewas refluxed for 3 hour
  2. filtrationThe solid particles were filtered off
  3. washThe filtrate was washed with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8515e883669c4c9b9c43643ba9d27aee
Source dataset
uspto-grants-2015_09
Patent number
US09126941B2

Reaction notes

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