5-Fluoro-2-nitrophenol → 2-Amino-5-fluorophenol

HRID 323018Notes

Reaction equation

HRID 323018 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([OH:8])[CH:7]=1.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[OH:8]

Participants

5

Reactant 3

HCID 99375-Fluoro-2-nitrophenolHCID 24479Stannous ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 1857632-Amino-5-fluorophenolYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-fluoro-2-nitrophenol (500 mg, 3.18 mmol) and tin (II) chloride (1.76 g, 9.2 mmol) in ethanol (10 mL) was heated at 80° C. under argon. After 30 min, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH 7-8), by addition of 5% aqueous sodium bicarbonate, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. Evaporation of the solvent gave the title compound (335 mg, 83%). 1H NMR (CD3OD/CDCl3): d 6.6 (m, 1H), 6.38 (dd, 1H, J=8.3 Hz and J=2.8 Hz), 6.29 (m, 1H).

Workup

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-341e42d56a8749a382c0a7a77f1c8b33
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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