Reaction #52341

Reaction equation

2-fluoro-iodo-phenyl acetic acid

Intermediate 3

2-Fluoro-4-iodo-phenyl acetic acid

sulfuric acid

ethanol

water

→

title compound

Yield 73.0%

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

Yield 73.0%

Solvents

benzene

hexane

ethyl acetate

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux overnight
3. 3
   workup.DISTILLATIONThe volatiles were distilled off in vacuo
4. 4
   workup.ADDITIONthe residue was diluted with water and diethyl ether
5. 5
   OtherThe phases were separated
6. 6
   Washthe organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1)
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated in vacuo
10. 10
    Otherto afford an oil which

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%).

Source