565-53-7 | Ethyl Dibromofluoroacetate

CAS:565-53-7 | Ethyl Dibromofluoroacetate ,Description

Ethyl dibromofluoroacetate (EDBFA) is an organofluorine compound and a derivative of dibromofluoroacetic acid. It is a colorless liquid with a strong odor and a melting point of -30.2 °C. It is a highly reactive compound and is used as a reagent in organic synthesis. EDBFA is also used in scientific research applications due to its ability to inhibit enzymes, interfere with cell metabolism, and cause cell death.
 

Scientific Research Applications

Synthesis of Fluorinated Glycidic Esters

Ethyl dibromofluoroacetate has been utilized in the synthesis of fluorinated glycidic esters. A study demonstrated the treatment of various ketones with ethyl dibromofluoroacetate in the presence of diethylzinc and dimethylaminoethanol or triphenylphosphine, facilitating rapid access to these compounds (Lemonnier et al., 2010).

Asymmetric Imino-Reformatsky Reaction

Ethyl dibromofluoroacetate is used in enantioselective Reformatsky reactions. An innovative ligand-promoted imino-Reformatsky approach with ethyl dibromofluoroacetate has been developed, enabling the synthesis of enantioenriched α-bromo-α-fluoro-β-lactams with high enantioselectivities (Tarui et al., 2014).

Preparation of α-Bromo-α-Fluoro-β-Hydroxyesters

Ethyl dibromofluoroacetate is effective in converting aldehydes, ketones, and lactones into α-bromo-α-fluoro-β-hydroxyesters. This application is significant for preparing building blocks in various synthetic processes (Zoute et al., 2011) .

Synthesis of Monofluorinated Cyclopropanes

A study described the use of ethyl dibromofluoroacetate for synthesizing monofluorinated cyclopropanes. The unique combination of Zn/LiCl enabled the generation of reactive zinc enolate from ethyl dibromofluoroacetate, which reacts efficiently with functionalized electron-deficient alkenes (Ivashkin et al., 2012).

Copper-Catalyzed N-Formylation of Amines

In another application, ethyl dibromofluoroacetate was used in the copper-catalyzed N-formylation of amines. This method was effective for a range of primary, secondary, cyclic arylamines, and aliphatic amines, providing N-formamides in moderate-to-excellent yields (Li et al., 2018).

Synthesis of gem-Halofluorocyclopropanes

A method for synthesizing gem-bromofluorocyclopropanes using ethyl dibromofluoroacetate was developed. This approach is efficient for creating bromofluorocyclopropane products, including multigram scales (Barrett et al., 2022).

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