Stannous Chloride → 3-Amino-2-fluoro-5-iodo-benzoic acid methyl ester

HRID 77764Notes

Reaction equation

HRID 77764 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[F:14].Cl[Sn]Cl>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[C:6]([NH2:11])[C:5]=1[F:14]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 57749798HCID 57749798, compound

Product 1

HCID 577498113-Amino-2-fluoro-5-iodo-benzoic acid methyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-5-iodo-3-nitro-benzoic acid methyl ester (1.0 g, 3.08 mmol) and SnCl2 (2.33 g, 12.3 mmol) were added to 20 mL EtOAc, and the mixture was heated to reflux for two hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in 20 mL saturated aqueous NaHCO3, and the aqueous mixture was extracted with EtOAc. The combined organic layers were washed with and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give 560 mg (62%) of 3-amino-2-fluoro-5-iodo-benzoic acid methyl ester, MS (M+H)=296.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for two hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in 20 mL saturated aqueous NaHCO3
  5. extractionthe aqueous mixture was extracted with EtOAc
  6. washThe combined organic layers were washed with and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b84afd7fee14d2cb367eac27148d83a
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Reaction notes

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