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

HRID 395024Notes

Reaction equation

HRID 395024 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 acidHCID 8857Ethyl AcetateHCID 222405322-(2-Fluoro-4-iodophenyl)acetonitrile2×

Product 1

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

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 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 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. 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-8048fd288c774e60ba27764eea9bb55f
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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