Chloride → 2-Amino-4-fluorophenol

HRID 1385425Notes

Reaction equation

HRID 1385425 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[Sn].[Cl-].[OH-].[Na+]>C(O)C>[NH2:9][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

6

Reactant 4

HCID 312ChlorideHCID 14798Sodium HydroxideHCID 1362364-Fluoro-2-nitrophenolHCID 5352426Tin atom

Product 1

HCID 27359172-Amino-4-fluorophenolYield 105.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-fluoro-2-nitrophenol (1 g, 4.64 mmol) and tin (to) chloride (5.4 g, 24.2 mmol) in ethanol (50 mL) was heated at 80° C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH is made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2Cl2) gave the desired product (622 mg, 85 %). 1H NMR (CD3, D): d 6.51 (dd, 1H), 6.32 (dd, 1H), 6.17 (ddd, 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. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b77a672bcd7d4b098c394b19708bdf08
Source dataset
uspto-grants-2001_07
Patent number
US06262113B1

Reaction notes

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