Réaction #52341

Équation de réaction

2-fluoro-iodo-phenyl acetic acid

Intermediate 3

2-Fluoro-4-iodo-phenyl acetic acid

sulfuric acid

ethanol

water

→

title compound

Rendement 73.0%

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

Rendement 73.0%

Solvants

benzene

hexane

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureat 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
   AutreThe phases were separated
6. 6
   Lavagethe organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1)
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated in vacuo
10. 10
    Autreto afford an oil which

Mode opératoire

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