반응 #1017456

반응 방정식

4-bromo-1-fluoro-2-iodobenzene

n-BuLi

Ethyl monofluoroacetate

→

title compound

수율 63.0%

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

수율 63.0%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction was stirred at −78° C. for one hour
2. 2
   기타The reaction was quenched with aqueous saturated ammonium chloride solution
3. 3
   온도to warm to RT
4. 4
   workup.ADDITIONThe reaction was diluted with water and EtOAc
5. 5
   기타The organic layer was separated
6. 6
   세척washed with brine
7. 7
   건조dried over magnesium sulfate
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The material was purified via silica gel flash chromatography

실험 절차

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

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