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
• Article Data: 4

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

• 667-27-6 Ethyl bromodifluoroacetate 
• 141-78-6 ethyl acetate 
• 1737-51-5 1-bromo-2-chloro-4,4-diethoxy-1,1,2-trifluoro-butane 
• 683-98-7 methyl bromodifluoroacetate 
• 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 
• 497845-56-4 ethyl 4,4-difluoro-5-phenyl-3-oxo-5-benzylamino-pentanoate 
• 1350908-57-4 4-[(bromo)(difluoro)methyl]-3-methyl-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4 b]pyridin-6-one 
• 1350908-59-6 4-[(bromo)(difluoro)methyl]-3-methyl-1-(4-methoxybenzyl)-6,7-dihydro-1H-pyrazolo[3,4 b]pyridin-6-one 
• 1350908-58-5 4-[(bromo)(difluoro)methyl]-1-(4-fluorophenyl)-3 methyl-6,7-dihydro-1H-pyrazolo[3,4 b]pyridin-6-one 
• 503812-32-6 ethyl 2-diazo-3-cyanomethylene-4,4-difluoro-5-(4-chlorophenyl)-5-(4-methoxyphenyl)amino-pentanoate 
• 503812-19-9 ethyl 2-diazo-4,4-difluoro-5-naphthyl-3-oxo-5-phenylamino-pentanoate 
• 503812-18-8 ethyl 2-diazo-4,4-difluoro-5-(4-chlorophenyl)-3-oxo-5-(4-methoxyphenyl)amino-pentanoate 
• 503812-33-7 ethyl 2-diazo-cyanomethylene-4,4-difluoro-5-phenyl-5-(benzyl)amino-pentanoate 

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.

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.