Methanol → Methyl 2-fluoro-6-iodobenzoate

HRID 1729499Notes

Reaction equation

HRID 1729499 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([I:16])[C:8]=1[C:9]([OH:11])=[O:10].[CH3:17]O>C(OCC)(=O)C>[F:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([I:16])[C:8]=1[C:9]([O:11][CH3:17])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric Acid2×HCID 27333022-Fluoro-6-iodobenzoic acid

Product 1

HCID 12192164Methyl 2-fluoro-6-iodobenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Concentrated sulphuric acid (0.5 ml) was added to a solution of 2-fluoro-6-iodobenzoic acid (1.03 g) in methanol (35 ml). After stirring at reflux for 5 days, with two further amounts of conc. sulphuric acid (1 ml) being added after 1 and 2 days, the solution was allowed to cool. The reaction mixture was diluted with ethyl acetate (200 ml) before being washed with water (2×80 ml), 8% aqueous sodium bicarbonate (2×100 ml), dried and concentrated in vacuo. Purification by chromatography eluting with System A (1:3) afforded the title compound (0.72 g) as an orange oil.

Workup

  1. additionbeing added after 1 and 2 days
  2. temperatureto cool
  3. washbefore being washed with water (2×80 ml), 8% aqueous sodium bicarbonate (2×100 ml)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography
  7. washeluting with System A (1:3)

Sources & evidence

ORD record
ord-9e872cbef28a4c92bafb834008cc3bc7
Source dataset
uspto-grants-1994_07
Patent number
US05332831

Reaction notes

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