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

HRID 1419343Notes

Reaction equation

HRID 1419343 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 (pH7-8), 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): δ6.6 (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-05d8826f65c7496ba609db5ff1036f62
Source dataset
uspto-grants-1999_03
Patent number
US05886044

Reaction notes

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