1,2-Difluoro-1,2-diphenylethane → 1,1-Difluoro-2,2-diphenylethane

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Reaction Steps

In a 15 mL fluoropolymer flask, 2,6-dimethyl-4-tert-butylphenylsulfur trifluoride (0.625 g, 2.5 mmol) was dissolved in 5 mL of anhydrous CH2Cl2. A solution of meso-1,2-diphenyl-1,2-ethanediol (0.214 g, 1.0 mmol) in 5 mL of anhydrous CH2Cl2 was added to the above stirred solution at room temperature. After 3 hours, C12H26F was added as standard, the 19F NMR analysis showed that 1,2-difluoro-1,2-diphenylethane (PhCHFCHFPh) was produced in 97% yield and a trace (˜0.03%) of 1,1-difluoro-2,2-diphenylethane (Ph2CHCF2H) was formed. Products were characterized by comparing to the spectroscopic data in literature (see Journal of Fluorine Chem. Vol. 125, pp 1869-1872 (2004)).

Provenance & Evidence