Reacción #1248532

Ecuación de reacción

hydrochloric acid

3-fluoro-4-nitrophenol

methyl 2,4-dibromobutyrate

potassium carbonate

→

title compound

Rendimiento 64.0%

4-Bromo-2-(3-fluoro-4-nitro-phenoxy)-butyric acid methyl ester

Rendimiento 64.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted
2. 2
   LavadoThe organic phases were washed with brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated
6. 6
   OtroThe residue was purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.)
7. 7
   Lavadoeluting with a gradient of heptane:ethyl acetate (1:0 to 1:1 v/v)

Procedimiento

To the solution of 5.5 g (35.0 mmol) 3-fluoro-4-nitrophenol in 55 mL N,N-dimethylformamide, 11.8 g (45.5 mmol) methyl 2,4-dibromobutyrate and 6.3 g (45.5 mmol) potassium carbonate were added. After stirring for 3 h the reaction mixture was poured on ethyl acetate and 1 M aqueous hydrochloric acid and extracted. The organic phases were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:ethyl acetate (1:0 to 1:1 v/v) to afford the title compound as a light yellow oil (64%) which was pure enough to be used in the next step.

Fuente