Methanol → HCID 57749798, compound

HRID 553780Notes

Reaction equation

HRID 553780 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 solution was washed with brine, dried over NaSO4, 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 solution was washed with brine
  5. dry with materialdried over NaSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d17a5eac188416fb8a9d27cfd3c4d9e
Source dataset
uspto-grants-2011_11
Patent number
US08048905B2

Reaction notes

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