Methanol → Methyl 5-fluoro-2-iodobenzoate

HRID 2174684Notes

Reaction equation

HRID 2174684 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([I:11])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:3]=[C:4]([C:8]([I:11])=[CH:9][CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

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

Product 1

HCID 53486126Methyl 5-fluoro-2-iodobenzoate

Procedure

To a solution of 3-fluoro-6-iodo benzoic acid (50 g; 0.18 mol) in methanol (220 ml) were added 10 ml of sulfuric acid and the mixture heated at reflux for 24 hours. After that the solvent was evaporated and the crude mixture diluted with water and extracted with dichloromethane (3×70 ml), the organic phases were collected, washed with bicarbonate (3×100 ml), dried over sodium sulphate and concentrated to yield the desired compound (51 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 hours
  3. customAfter that the solvent was evaporated
  4. additionthe crude mixture diluted with water
  5. extractionextracted with dichloromethane (3×70 ml)
  6. customthe organic phases were collected
  7. washwashed with bicarbonate (3×100 ml)
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bcac7cce355c41cc99d2ba55920fe80e
Source dataset
uspto-grants-2015_06
Patent number
US09062033B2

Reaction notes

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