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

HRID 1433338Notes

Reaction equation

HRID 1433338 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>C(OCC)(=O)C.O1CCCC1.[C].[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([OH:11])=[CH:3][C:2]=1[F:1]

Participants

5

Procedure

3-Fluoro-4-nitrophenol (5.0 g, 31.83 mmol) was dissolved in ethyl acetate (50 ml) and tetrahydrofuran (75 ml), and then palladium carbon (2.0 g) was added and the mixture was stirred for 8.5 hours at room temperature under a hydrogen atmosphere. The catalyst was filtered off, the filtrate was washed with ethanol, the solvent was distilled off under reduced pressure and the obtained crystals were washed with addition of hexane:ethanol=1:1. The crystals were filtered out, washed with diethyl ether and dried by aspiration to obtain the title compound (1.62 g, 12.74 mmol, 40.61%) as light yellow crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. washthe filtrate was washed with ethanol
  3. distillationthe solvent was distilled off under reduced pressure
  4. washthe obtained crystals were washed with addition of hexane
  5. filtrationThe crystals were filtered out
  6. washwashed with diethyl ether
  7. customdried by aspiration

Sources & evidence

ORD record
ord-d8feeb53b22f4bbfb1b97757485cb0ed
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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