Methanol → HCID 57749798, compound

HRID 77763Notes

Reaction equation

HRID 77763 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([I:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O=S(Cl)Cl.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([I:14])[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[F:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 57749803HCID 57749803, compound

Product 1

HCID 57749798HCID 57749798, compoundYield 96%

Procedure

2-Fluoro-5-iodo-3-nitro-benzoic acid (2.0 g, 6.43 mmol) and SOCl2 (918 mg, 7.72 mmol) were added to 20 mL MeOH, and the mixture was refluxed for two hours and then cooled to room temperature. Solvent was evaporated under reduced pressure and the residue was dissolved in EtOAa. The EtOAc slolution was washed with brine, dried over NasSO4, filtered and concentrated under reduced pressure to give 2.0 g (96%) of 2-fluoro-5-iodo-3-nitro-benzoic acid methyl ester.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. customSolvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in EtOAa
  4. washThe EtOAc slolution was washed with brine
  5. customdried over NasSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a00ea54da970414c8701fa302f601d74
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Reaction notes

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