Reacción #79906

Ecuación de reacción

2-fluoro-iodo-phenyl acetic acid

Intermediate 3

2-Fluoro-4-iodo-phenyl acetic acid

sulfuric acid

ethanol

water

→

title compound

Rendimiento 73.0%

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

Rendimiento 73.0%

Disolventes

benzene

hexane

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat 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
   OtroThe phases were separated
6. 6
   Lavadothe organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1)
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated in vacuo
10. 10
    Otroto afford an oil which

Procedimiento

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%).

Fuente