反応 #52341

反応方程式

2-fluoro-iodo-phenyl acetic acid

Intermediate 3

2-Fluoro-4-iodo-phenyl acetic acid

sulfuric acid

ethanol

water

→

title compound

収率 73.0%

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

収率 73.0%

溶媒

benzene

hexane

ethyl acetate

反応条件

後処理

1. 1
   温度heated
2. 2
   温度at 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
   その他The phases were separated
6. 6
   洗浄the organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1)
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   その他evaporated in vacuo
10. 10
    その他to afford an oil which

実験手順

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%).

出典