The rapid and efficient difluoromethylation of a panel of 11 bisphenols (BPs) for their enhanced detection and identification by Electron-Impact Gas Chromatography-Mass Spectrometry (EI-GC-MS) is presented.  The derivatization employs the inexpensive, environmentally benign agent diethyl (bromodifluoromethyl) phosphonate (DBDFP) as a difluorocarbene-generating species that converts the BPs into their <i>bis</i>-difluoromethylated ethers that can be detected and identified by GC-MS means.  Key attributes of the protocol include its extreme rapidity (30 seconds) at ambient temperature, high specificity for BPs amidst other alcohol-containing analytes, and its biphasic nature that allows for its convenient adaptation to the analysis of BPs in organic as well as aqueous matrices.  The protocol furnishes stable, novel BP ethers armed with a total of four fluorine atoms for their subsequent analysis by EI-GC-MS.  The effectiveness and robustness of the methodology was applied to the successful tagging and detection of the most famous member of this family of compounds, bisphenol-A (BPA), when spiked (at 1 μg g<sup>-1</sup>concentration) in three representative soils: Virginia type A soil, Nebraska EPA soil, and Ottawa sand.

Diethyl(bromodifluoromethyl) phosphonate as a versatile reagent for the difluoromethylation of bisphenols for their detection and identification by gas chromatography-mass spectrometry

2019 Fall National Meeting

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