Reaktion #52341

Reaktionsgleichung

2-fluoro-iodo-phenyl acetic acid

Intermediate 3

2-Fluoro-4-iodo-phenyl acetic acid

sulfuric acid

ethanol

water

→

title compound

Ausbeute 73.0%

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

Ausbeute 73.0%

Lösungsmittel

benzene

hexane

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat 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
   SonstigeThe phases were separated
6. 6
   Waschenthe organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1)
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated in vacuo
10. 10
    Sonstigeto afford an oil which

Vorschrift

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%).

Quelle