Ethyl fluoroacetate → 1-(5-Bromo-2-fluorophenyl)-2-fluoroethanone

Temperature

-78 °C

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

1. stirringthe reaction was stirred at −78° C. for one hour
2. customThe reaction was quenched with aqueous saturated ammonium chloride solution
3. temperatureto warm to RT
4. additionThe reaction was diluted with water and EtOAc
5. customThe organic layer was separated
6. washwashed with brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe material was purified via silica gel flash chromatography

ORD record

ord-f31efca221ea4359a3a43617e7784d7f

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296734B2