401-55-8

Usage

Uses

Used in Chemical Synthesis:
Ethyl bromofluoroacetate is used as an intermediate for the synthesis of polyfluoroalkyl-substituted fluoro enol ethers. These enol ethers are valuable in the creation of various chemical compounds due to their unique properties and reactivity.
Ethyl bromofluoroacetate is also used as an intermediate in the synthesis of N-protected α-fluoroglycines. These α-fluoroglycines are important building blocks in the development of pharmaceuticals, particularly in the design of new drugs with potential therapeutic applications.

InChI:InChI=1/C4H6BrFO2/c1-2-8-4(7)3(5)6/h3H,2H2,1H3/t3-/m0/s1

Upstream product

• 380-78-9 1-ethoxy-1,1,2-trifluoro-2-bromoethane 
• 623-73-4 diazoacetic acid ethyl ester 
• 2707-82-6 Diethyl 2-bromo-2-fluoro-3-oxobutanedioate 
• 64-17-5 ethanol 

Downstream Products

• 359-25-1 bromo-fluoroacetic acid 
• 20397-61-9 (Z)-2-fluoro-3-phenylacrylic acid 
• 66183-24-2 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-erythro-hex-3-ulo-1-enitol 
• 78468-51-6 (S)-Fluoro-((2R,4aR,6S,8S,8aR)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-acetic acid methyl ester 
• 78468-50-5 methyl 4,6-O-benzylidene-2-deoxy-3-C-<(S)-(ethoxycarbonyl)fluoromethyl>α-D-ribo-hexopyranoside 
• 78468-50-5 methyl 4,6-O-benzylidene-2-deoxy-3-C-<(R)-(ethoxycarbonyl)fluoromethyl>α-D-ribo-hexopyranoside 
• 78468-51-6 (R)-Fluoro-((2R,4aR,6S,8S,8aR)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-acetic acid methyl ester 
• 78468-50-5 (R)-Fluoro-((2R,4aR,6S,8R,8aR)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-acetic acid ethyl ester 
• 108221-62-1 α-Phenyl-γ-fluorotetronic acid 
• 108221-64-3 3-fluoro-5-(4-methoxyphenyl)-2,4(3H,5H)-furandione 
• 100366-22-1 Ethyl Benzoyloxyfluoroacetate 
• 132629-29-9 N,N-bis(benzyloxycarbonyl)-α-fluoroglycine ethyl ester 
• 401-58-1 ethyl 2-fluoro-2-iodoacetate 
• 430-91-1 bromofluoroacetamide 

Relevant academic research and scientific papers

Tetrafluorine-containing ketones and acetoacetates: Synthesis and mechanistic study

Addition of trimethylsilyl trifluoroacetate to the carbanions of α-fluorobenzyl-phosphonate (3) or diisopropyl(fluorocarbethoxymethyl) phosphonate (9) formed the corresponding intermediates [CF3C(O)CFPh] -Li+ (10) and [CF3C(O)CFCO2Et] -Li+ (11), respectively. Subsequent protonation, alkylation or allylation of 10 and 11 afforded trifluoromethyl fluorobenzyl ketones 12 and ethyl 2,4,4,4-tetra-fluoroacetoacetates 13. Based on the results obtained, a plausible mechanism was proposed.

Synthesis of phenyl and ester substituted vinyl fluorides via reduction and olefination of esters

A reduction-olefination sequence has been used to convert ethyl pentafluoropropanoate 6 to 1-fluoro-1-phenyl-2-pentafluoroethyl ethene 7 and ethyl 2,4,4,5,5,5-hexafluoro-2-pentenoate 8. Addition of lithium diethyl α-fluorobenzylphosphonate [(EtO)2P(O)CFPh]- Li+ 4 or lithium fluorocarboethoxymethylene dialkylphosphonate [(RO)2P(O)CFCO2Et]- Li+ 5 (R = Et, i-Pr) to a THF solution of fluorinated aldehydes prepared in situ from 6 and diisobutylaluminum hydride (DIBAL) affords the vinyl fluorides C2F5CH=CFPh 7 and C2F5CH=CFCO2Et 8 in good yields. However, yields of the final products 7 and 8 are low when in situ reduction of 6 to aldehyde was performed in the presence of lithium salts of 4 or 5.

Application of fluorocarbethoxy-substituted phosphonate: A facile entry to substituted 2-fluoro-3-oxoesters

Diethyl(fluorocarbethoxymethyl)phosphonate 1a or diisopropyl(fluorocarbethoxymethyl)phosphonate 1b, prepared from triethyl phosphite or triisopropyl phosphite with ethyl bromofluoroacetate, react with n-butyllithium in THF to give the corresponding phosphonate carbanions [(RO)2P(O)CFCO2Et]-Li+ 2a (R = Et) and 2b (R = i-Pr). Addition of trimethylsilyltrifluoroacetate CF3C(O)OSiMe3 to a THF solution of phosphonate carbanions formed the enolate of ethyl trifluoroacetylfluoroacetate [CF3C(O)CFCO2Et]-Li+ 3. Subsequent protonation, alkylation or allylation of the enolate afforded substituted 2,4,4,4-tetrafluoro-3-oxoesters CF3C(O)CFR1CO2Et 10.

A Convenient Synthesis of Ethyl (Diethoxyphosphoryl)fluoroacetate from Ethyl Fluoroacetate

A new synthesis of ethyl (diethoxyphosphoryl)fluoroacetate starting from ethyl fluoroacetate is described for a mole scale.This synthesis does not require the use of special equipment for fluorine chemistry since no hydrogen fluoride is evolved.