Methanol → Methyl 5-fluoro-2-iodobenzoate

HRID 1971832Notes

Reaction equation

HRID 1971832 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[OH-].[Na+].[CH3:19]O>>[CH3:19][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[I:11]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 131585835-Fluoro-2-iodobenzoic acid

Product 1

HCID 53486126Methyl 5-fluoro-2-iodobenzoateYield 98%

Procedure

A mixture of 5-fluoro-2-iodo-benzoic acid (10.05 g, 39.47 mmol) and conc. H2SO4 (10 mL) in MeOH (100 ml) was reflux for 6 hours. After cooling to room temperature, NaOH (2N) was added dropwise to adjust the pH˜8. After most of organic solvent was removed under reduced pressure, the mixture was extracted with dichloromethane three times. The combined organic layers were washed with water, dried and concentrated to give the titled compound (10.80 g, yield 98%)

Workup

  1. temperaturewas reflux for 6 hours
  2. customAfter most of organic solvent was removed under reduced pressure
  3. extractionthe mixture was extracted with dichloromethane three times
  4. washThe combined organic layers were washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b809cd07a3684f20b019cadc15329a29
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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