Methanol → Methyl 2-(4-fluoro-2-iodophenyl)acetate

HRID 1711086Notes

Reaction equation

HRID 1711086 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([I:12])[CH:3]=1.S(=O)(=O)(O)O.[CH3:18]O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:18])=[O:10])=[C:4]([I:12])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 125201654-Fluoro-2-iodophenylacetic acid

Product 1

HCID 59457703Methyl 2-(4-fluoro-2-iodophenyl)acetateYield 95%

Procedure

A solution of the acid 324 (3.95 g, 14.1 mmol) and sulfuric acid (0.5 mL) in methanol (50 mL) was heated under reflux for 18 h, then cooled and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water; the organic phase was collected, dried (anhydrous MgSO4), filtered and concentrated to afford pure 325 (3.93 g, 95% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.57 (dd, J=8.2, 2.7 Hz, 1H); 7.25 (dd, J=8.6, 5.9 Hz, 1H); 7.05 (dt, J=8.2, 2.7 Hz, 1H); 3.78 (s, 2H); 3.72 (s, 3H). LCMS: (M+H) 295.0.

Workup

  1. temperatureunder reflux for 18 h
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic phase was collected
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4f6113d5dd6149e9a76988c1c56ba4f1
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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