Stannous Chloride → 4,5-Dichloro-2-fluoroaniline

HRID 1907105Notes

Reaction equation

HRID 1907105 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([F:14])=[CH:7][C:6]=1[Cl:15].C(=O)(O)[O-].[Na+]>C(O)C>[Cl:15][C:6]1[C:5]([Cl:4])=[CH:10][C:9]([NH2:11])=[C:8]([F:14])[CH:7]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 5339511,2-Dichloro-4-fluoro-5-nitrobenzene

Product 1

HCID 2230914,5-Dichloro-2-fluoroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin (II) chloride dehydrate (27.0 g, 119.6 mmol) was dissolved in ethanol and 1,2-dichloro-4-fluoro-5-nitrobenzene (5.0 g, 23.8 mmol) was added dropwise. Temperature rose to near reflux during the addition and was complete upon cooling. The reaction mixture was carefully added to saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. The organic phase was washed several more times with water, dried, filtered and concentrated to give the title compound as a yellow solid: 1H NMR (CDCl3): δ 7.17 (d, 1H), 6.84 (d, 1H), 3.78 (br s, 2H).

Workup

  1. temperatureto near reflux during the addition
  2. temperatureupon cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed several more times with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e86de8df2a6547c6adc88e09636516d6
Source dataset
uspto-grants-2013_12
Patent number
US08598085B2

Reaction notes

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