Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate → Phenyl dibenzothiophenium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate

Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate (4.00 g, 12.1 mmol) and phenyl dibenzothiophenium bromide (4.50 g, 31.2 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. Stirring was stopped and the mixture separated into two clear layers; the organic layer was washed twice with 30 mL 1% aqueous hydrochloric acid and five times with 30 mL of distilled, de-ionized water. Hydroquinone (1 mg) was added and dichloromethane was removed by rotary evaporation to yield the product as a solid (3.9 g, 80% yield). 1H NMR (500 MHz, CDCl3) δ 8.2 (m, 4H), 7.8 (t, 2H), 7.7 (d, 2H), 7.6 (m, 3H), 7.5 (t, 2H), 6.2 (s, 1H), 5.6 (s, 1H), 4.9 (m, 2H), 1.9 (s, 3H). 19F NMR (300 MHz, acetone-d6) δ −115.8 (s, 2F).