Ethanol → Ethyl-2-fluoro-4-iodo-phenyl acetate

HRID 381019Notes

Reaction equation

HRID 381019 reaction equation
FC([I:12])(C1C=CC=CC=1)C(O)=O.[F:13][C:14]1[CH:19]=[C:18](I)[CH:17]=[CH:16][C:15]=1[CH2:21][C:22](O)=O.S(=O)(=O)(O)O.[OH2:30].[CH2:31]([OH:33])[CH3:32]>C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[C:31]([O:33][C:19]1[CH:18]=[CH:17][C:16]([I:12])=[C:15]([CH2:21][CH3:22])[C:14]=1[F:13])(=[O:30])[CH3:32]

Participants

9

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 222403932-(2-Fluoro-4-iodophenyl)acetic acidHCID 225689092-Fluoro-iodo-phenyl acetic acid

Product 1

HCID 69548701Ethyl-2-fluoro-4-iodo-phenyl acetateYield 73%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-fluoro-iodo-phenyl acetic acid (Intermediate 3, 1.75 g, 6.22 mmol) in ethanol (50 mL) and benzene (100 mL) was treated with concentrated sulfuric acid (1.4 mL) and heated at reflux overnight using a Dean-Stark water trap. The volatiles were distilled off in vacuo and the residue was diluted with water and diethyl ether. The phases were separated and the organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 5%-10% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow solid (1.4 g, 73%).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. distillationThe volatiles were distilled off in vacuo
  4. additionthe residue was diluted with water and diethyl ether
  5. customThe phases were separated
  6. washthe organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto afford an oil which

Sources & evidence

ORD record
ord-336bb013eb3c491f9c3f0fd23b1876f0
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

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