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

HRID 553781Notes

Reaction equation

HRID 553781 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-d2c803eb6ffd4f5caf3011946e91f8a6
Source dataset
uspto-grants-2011_11
Patent number
US08048905B2

Reaction notes

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