367922-07-4

Basic information

• Product Name: Ethyl 4-bromo-4,4-difluoro-3-oxobutanoate, Ethyl 4-bromo-4,4-difluoro-3-oxobutyrate
• Synonyms: Ethyl 4-bromo-4,4-difluoro-3-oxobutanoate, Ethyl 4-bromo-4,4-difluoro-3-oxobutyrate;Ethyl 4-bromo-4,4-difluoroacetoacetate
• CAS NO: 367922-07-4
• Molecular Formula: C₆H₇BrF₂O₃
• Molecular Weight: 245.0187864
• Mol File: 367922-07-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl 4-bromo-4,4-difluoro-3-oxobutanoate, Ethyl 4-bromo-4,4-difluoro-3-oxobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-bromo-4,4-difluoro-3-oxobutanoate, Ethyl 4-bromo-4,4-difluoro-3-oxobutyrate(367922-07-4)
• EPA Substance Registry System: Ethyl 4-bromo-4,4-difluoro-3-oxobutanoate, Ethyl 4-bromo-4,4-difluoro-3-oxobutyrate(367922-07-4)

Safety Data

• Hazardous Substances Data: 367922-07-4(Hazardous Substances Data)

Upstream product

• 683-98-7 methyl bromodifluoroacetate 
• 141-78-6 ethyl acetate 
• 667-27-6 Ethyl bromodifluoroacetate 
• 1737-51-5 1-bromo-2-chloro-4,4-diethoxy-1,1,2-trifluoro-butane 
• 367922-09-6 4-bromo-3-chloro-3,4,4-trifluoro-butyric acid ethyl ester 
• 144850-56-6 ethyl 4-bromo-3,3,4,4-tetrafluorobutanoate 

Downstream Products

• 352-24-9 ethyl 4,4-difluoro-3-oxobutyrate 
• 497845-65-5 ethyl 4,4-difluoro-5-phenyl-3-oxo-5-phenylamino-hexanoate 

Relevant articles and documents

IMPROVED PROCESS FOR PREPARING SUBSTITUTED CROTONIC ACIDS

A process to prepare a compound of Formula (I) wherein R3, R4 and R5 are each selected independently from hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxyl, and wherein the alkyl, alkenyl, alkynyl, and alkoxyl may be optionally substituted with one or more halogen, alkyl, alkenyl, alkynyl, and alkoxyl.

Synthesis of new fluorine-containing pyrazolo[3,4-b]pyridinones as promising drug precursors

Methods for the synthesis of 4-R-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-6- ones (R = CF2SAr and 4-CFHSAr) were developed. The derivatives with R = CF2SAr were obtained by both heterocyclization of 1-substituted 5-aminopyrazoles with ethyl 4,4-difluoro-3-oxo-4-phenylsulfanylbutanoate and replacement of the Br atom in 4-bromodifluoromethyl-6,7-dihydro-1H-pyrazolo[3,4- b]pyridin-6-ones by sodium arenethiolates. The fragment 4-CF-HSAr was introduced by replacement of the Cl atom in 4-chlorofluoromethyl-6,7-dihydro-1H- pyrazolo[3,4-b]pyridin-6-ones by sodium arenethiolates. Oxidation of 4-CF 2SPh-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-6-ones gave the corresponding sulfoxides; their structures were confirmed by X-ray diffraction data.

Studies on a three-step preparation of β-fluoroalkyl acrylates from fluoroacetic esters

β-Fluoroalkyl-acrylic esters are valuable building blocks for the synthesis of organofluorine compounds. Although the preparation of several β-fluoroalkyl-acrylates is known, a general and straightforward lab-scale methodology for the preparation of multigram amounts of these compounds from fluoroacetic esters is not available, and the related chemistry has not been investigated in detail. We now describe an optimized three-step protocol relying on: (1) Claisen-type condensation of fluoroacetic esters with ethyl acetate, using LDA as base; (2) reduction of the resulting γ-fluoro-β-keto esters by NaBH4, using toluene or benzene as solvents; (3) P2O5-promoted dehydration of the intermediate γ-fluoro-β-hydroxy esters. The methodology affords preparatively useful yields of the target compounds incorporating only fluorine atoms (CF3, CHF2, C2F5), whereas the γ-halodifluoromethyl (CClF2, CBrF2, CIF2) acrylates could not be obtained in analytically pure form from the dehydration step.

Reformatsky-type aldol reactions of 4-bromo-4,4-difluoroacetoacetate with aldehydes and ketones

In the presence of zinc and a catalytic amount of copper(I) chloride, 4-bromo-4,4-difluoroacetoacetate 4 reacted with a series of aromatic aldehydes and aryl alkyl ketones to give the corresponding δ-hydroxyl-γ,γ-difluoro-β-ketoesters 6 in good to excellent yields under mild conditions.