Stannous Chloride → 5-Bromo-2-fluoroaniline

HRID 2218628Notes

Reaction equation

HRID 2218628 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.Cl[Sn]Cl>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([NH2:9])[CH:3]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 27694075-Bromo-2-fluoroanilineYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 4-bromo-1-fluoro-2-nitrobenzene (5.00 g, 22.73 mmol) and SnCl2 (dihydrate, 25.46 g, 113.6 mmol) in ethanol (100 mL) and heat to reflux overnight. Cool to room temperature and concentrate in-vacuo. Dissolve residue in ethyl acetate and basify with saturated aqueous NaHCO3. Filter through a pad of Celite and extract filtrate with ethyl acetate. Dry (MgSO4) and concentrate organics to a brown oil. Chromatograph on 90 g silica gel, eluting with 5% to 10% ethyl acetate/hexanes affords 2.85 g (66%) of the title compound as a tan oil. MS (ES) 191 (M+H); HPLC shows 99% purity.

Workup

  1. temperatureheat
  2. temperatureto reflux overnight
  3. concentrationconcentrate in-vacuo
  4. filtrationFilter through a pad of Celite
  5. extractionextract filtrate with ethyl acetate
  6. dry with materialDry (MgSO4)
  7. concentrationconcentrate organics to a brown oil
  8. washChromatograph on 90 g silica gel, eluting with 5% to 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b3c3774800b84db0a44c2b4a921769e6
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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