Water → Methyl-2-fluoro-4-iodo-phenyl acetate

HRID 427776Notes

Reaction equation

HRID 427776 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=CC=1CC#N.[C:12]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH2:23].[C:24]([O:27][CH2:28][CH3:29])(=O)[CH3:25]>CO.C1C=CC=CC=1.CCCCCC>[C:28]([O:27][C:24]1[CH:25]=[CH:5][C:6]([I:8])=[C:7]([CH3:12])[C:2]=1[F:1])(=[O:23])[CH3:29]

Participants

8

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acid2×HCID 8857Ethyl AcetateHCID 222405322-(2-Fluoro-4-iodophenyl)acetonitrile2×

Product 1

HCID 69548383Methyl-2-fluoro-4-iodo-phenyl acetateYield 80%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 887MethanolSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 2-fluoro-4-iodo-phenyl acetonitrile (Intermediate 2, 3 g, 11.45 mmol) in methanol (50 mL) and benzene (50 mL) was treated with p-toluene sulfonic acid (2.5 g, 13.15 mmol) and heated at reflux overnight using a 11.45 mmol) in methanol (50 mL) and benzene (50 mL) was treated with p-toluene sulfonic acid (2.5 g, 13.15 mmol) 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 6% ethyl acetate in hexane as the eluent to afford the title compound as a colorless oil (2.7 g, 80%).

Workup

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

Sources & evidence

ORD record
ord-658bd82a64f34e0aba4b24225ec57244
Source dataset
uspto-grants-2001_11
Patent number
US06313107B1

Reaction notes

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