Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate → (t-Butylphenyl)(phenyl)iodonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate

Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate (5.00 g, 15.1 mmol) and (t-butylphenyl)(phenyl)iodonium acetate (5.98 g, 15.1 mmol) were added to a 100 mL round bottom flask, along with 30 mL of dichloromethane and 30 mL of distilled, de-ionized water. The mixture was stirred vigorously overnight, then stopped and the mixture separated into two clear layers; the organic layer was washed once with 30 mL 1% (w/w) aqueous hydrochloric acid and four times with 30 mL of de-ionized water. Hydroquinone (1 mg) was added and dichloromethane removed by rotary evaporation to yield the product as a colorless, viscous oil (7.6 g, 89% yield). The oil was dissolved to 50 wt % in acetonitrile. 1H NMR (500 MHz, acetone-d6) δ 8.4 (d, 2H), 8.3 (d, 2H), 7.7 (t, 1H), 7.6 (m, 4H), 6.2 (s, 1H), 5.7 (s, 1H), 4.7 (m, 2H), 1.9 (s, 3H), 1.3 (s, 9H). 19F NMR (300 MHz, acetone-d6) δ −115.4 (s, 2F).