Synthesis, characterisation and mass spectrometric fragmentation of O-(chlorodifluoroacylated) alcohols

• Published in: Journal of fluorine chemistry Vol. 113; no. 1; pp. 47 - 50
• Main Authors: Bhadury, Pinaki S., Palit, Meehir, Sharma, Mamta, Raza, Syed K., Jaiswal, Devendra K.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 28.01.2002; Elsevier
• Subjects: 19F NMR; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Esterification; Mass spectrometric fragmentation; Physical Sciences; Polyfluorinated alcohols; Science & Technology; Sodium chlorodifluoroacetate; Tandem mass spectrometry; Tandem mass spectrometry; Polyfluorinated alcohols; Sodium chlorodifluoroacetate; Esterification; 19F NMR; Mass spectrometric fragmentation; F-19 NMR; tandem mass spectrometry; polyfluorinated alcohols; sodium chlorodifluoroacetate; esterification; mass spectrometric fragmentation
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/S0022-1139(01)00465-1

An indirect and uncatalysed esterification of chlorodifluoroacetic acid with polyfluoro and hydrocarbon alcohols has been developed. The method which involves the reaction between sodium chlorodifluoroacetate and alcohols in dimethylformamide (DMF) is particularly facile with polyfluorinated alcohols resulting in esters in 71–85% yield. The esters have been characterised on the basis of 1H and 19F NMR and mass spectral data. The electron impact (EI) mass spectrometric fragmentation of these polyfluorinated esters have shown some interesting features which have been substantiated by using tandem mass spectrometry.