反応 #1017456

反応方程式

4-bromo-1-fluoro-2-iodobenzene

n-BuLi

Ethyl monofluoroacetate

→

title compound

収率 63.0%

1-(5-bromo-2-fluorophenyl)-2-fluoroethanone

収率 63.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction was stirred at −78° C. for one hour
2. 2
   その他The reaction was quenched with aqueous saturated ammonium chloride solution
3. 3
   温度to warm to RT
4. 4
   workup.ADDITIONThe reaction was diluted with water and EtOAc
5. 5
   その他The organic layer was separated
6. 6
   洗浄washed with brine
7. 7
   乾燥dried over magnesium sulfate
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他The material was purified via silica gel flash chromatography

実験手順

A solution of 4-bromo-1-fluoro-2-iodobenzene (5.0 g, 116 mmol, (1), Aldrich) in THF (60 ml) under nitrogen atmosphere was cooled to −78° C. A solution of n-BuLi (2.5M in hexanes; 7.31 ml, 18.28 mmol, Aldrich) was added drop wise and the reaction was stirred at −78° C. for one hour. Ethyl monofluoroacetate (2.1 g, 19.94 mmol, Aldrich) was added drop wise and the reaction was stirred at −78° C. for one hour. The reaction was quenched with aqueous saturated ammonium chloride solution and allowed to warm to RT. The reaction was diluted with water and EtOAc. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The material was purified via silica gel flash chromatography using a gradient of 0-20% EtOAc in Hexanes to afford the title compound as an off white solid. (2.45 g, 10.42 mmol, 63% yield). MS m/z=234.9 M+. Calculated for C8H5BrF2O: 235.03

出典