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

HRID 1927371Notes

Reaction equation

HRID 1927371 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-6ed5f3850bab48eb8bc7956c4c58ecef
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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