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

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Reaction Steps

To the solution of 5.5 g (35.0 mmol) 3-fluoro-4-nitrophenol (CAS Reg. No. 399-95-1) in 55 mL N,N-dimethylformamide, 11.8 g (45.5 mmol) methyl 2,4-dibromobutyrate (CAS Reg. No. 29547-04-4) 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.

Provenance & Evidence