Fluorination of Methyl 3-Oxopentanoate (MOP) Using Difluorobis(fluoroxy)methane, BDM

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Title:Fluorination of Methyl 3-Oxopentanoate (MOP) Using Difluorobis(fluoroxy)methane, BDM
Creators:
Bailey III, Wade H.
Casteel, William J.
Syvret, Robert G.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 10, pp. 1416-1420
Uncontrolled Keywords:Keto esters, Fluoroxy compounds, Electrophilic fluorination, Fluorinated compounds, Dicarbonyl fluorination

Abstract

Difluorobis(fluoroxy)methane, BDM, is an electrophilic fluorinating agent that is capable of affecting selective monofluorination of 1,3-dicarbonyls such as diketones and ketoesters with very high regioselectivity. For example, in highly acidic anhydrous HF (AHF) solvent, fluorination of methyl 3-oxopentanoate (MOP) with BDM provides methyl 2-fluoro-3-oxopentanoate (MFOP) with 100% conversion and 95% selectivity. In mixtures of HF and methanol, fluorination conversions and selectivity are markedly lower. In comparison, direct fluorination of MOP with dilute F<sub>2</sub> typically affords a fluorinated product that is less pure, being contaminated with radical fluorination byproducts that are difficult to separate. Fluorination of MOP with dilute mixtures of BDM and F<sub>2</sub> is generally more selective than using dilute F<sub>2</sub> alone. <p>

Title:Fluorination of Methyl 3-Oxopentanoate (MOP) Using Difluorobis(fluoroxy)methane, BDM
Creators:
Bailey III, Wade H.
Casteel, William J.
Syvret, Robert G.
Uncontrolled Keywords:Keto esters, Fluoroxy compounds, Electrophilic fluorination, Fluorinated compounds, Dicarbonyl fluorination
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:10
Page Range:pp. 1416-1420
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021416UNSPECIFIED
ID Code:2003
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Bailey III, Wade H.; Casteel, William J.; Syvret, Robert G. (2002) Fluorination of Methyl 3-Oxopentanoate (MOP) Using Difluorobis(fluoroxy)methane, BDM. Collection of Czechoslovak Chemical Communications, 67 (10). pp. 1416-1420. ISSN 0010-0765

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