1,1,2,2-tetrafluoroethoxybenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 50 mL flask equipped with a stir-bar and a nitrogen bubbler was charged with concentrated sulfuric acid (14.55 g) and 4-(1,1,2,2-tetrafluoroethoxy)benzene (4.9 g) at room temperature. The reaction mixture was stirred at room temperature for 17 h. A sodium hydroxide solution (12.25 g, in 40.02 g water) was slowly added to the reaction mixture while the reaction mixture was cooled with an ice-water bath. The resulting solid was filtered off. The filtrate was neutralized with concentrated hydrochloric acid (˜3 mL) and used to wash the solid. This wash solution was neutralized with sodium bicarbonate to pH˜7, and used to wash the solid again. The solid was extracted with refluxing ethanol. The ethanol solution was dried to give sodium 4-(1,1,2,2-tetrafluoroethoxy)benzenesulfonate (4FEBSNa) 4.4 g (yield 59%): 1H NMR (D2O) 6.34 (tt, 52, 3 Hz, 1H), 7.45 (d, J=9 Hz, 2H), 7.88 (m, 2H) ppm; 19F NMR (D2O) −88.7 (m, 2F), −138.0 (dt, J=52, 5 Hz, 2F) ppm. A 50 mL flask equipped with a stir-bar was cooled with an ice-water bath The resulting solid was filtered off to wash the solid to wash the solid again The solid was extracted with refluxing ethanol The ethanol solution was dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 50 mL flask equipped with a stir-bar and a nitrogen bubbler was charged with concentrated sulfuric acid (14.55 g) and 4-(1,1,2,2-tetrafluoroethoxy)benzene (4.9 g) at room temperature. The reaction mixture was stirred at room temperature for 17 h. A sodium hydroxide solution (12.25 g, in 40.02 g water) was slowly added to the reaction mixture while the reaction mixture was cooled with an ice-water bath. The resulting solid was filtered off. The filtrate was neutralized with concentrated hydrochloric acid (˜3 mL) and used to wash the solid. This wash solution was neutralized with sodium bicarbonate to pH˜7, and used to wash the solid again. The solid was extracted with refluxing ethanol. The ethanol solution was dried to give sodium 4-(1,1,2,2-tetrafluoroethoxy)benzenesulfonate (4FEBSNa) 4.4 g (yield 59%): 1H NMR (D2O) 6.34 (tt, 52, 3 Hz, 1H), 7.45 (d, J=9 Hz, 2H), 7.88 (m, 2H) ppm; 19F NMR (D2O) −88.7 (m, 2F), −138.0 (dt, J=52, 5 Hz, 2F) ppm. A 50 mL flask equipped with a stir-bar was cooled with an ice-water bath The resulting solid was filtered off to wash the solid to wash the solid again The solid was extracted with refluxing ethanol The ethanol solution was dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 50 mL flask equipped with a stir-bar and a nitrogen bubbler was charged with concentrated sulfuric acid (14.55 g) and 4-(1,1,2,2-tetrafluoroethoxy)benzene (4.9 g) at room temperature. The reaction mixture was stirred at room temperature for 17 h. A sodium hydroxide solution (12.25 g, in 40.02 g water) was slowly added to the reaction mixture while the reaction mixture was cooled with an ice-water bath. The resulting solid was filtered off. The filtrate was neutralized with concentrated hydrochloric acid (˜3 mL) and used to wash the solid. This wash solution was neutralized with sodium bicarbonate to pH˜7, and used to wash the solid again. The solid was extracted with refluxing ethanol. The ethanol solution was dried to give sodium 4-(1,1,2,2-tetrafluoroethoxy)benzenesulfonate (4FEBSNa) 4.4 g (yield 59%): 1H NMR (D2O) 6.34 (tt, 52, 3 Hz, 1H), 7.45 (d, J=9 Hz, 2H), 7.88 (m, 2H) ppm; 19F NMR (D2O) −88.7 (m, 2F), −138.0 (dt, J=52, 5 Hz, 2F) ppm. A 50 mL flask equipped with a stir-bar was cooled with an ice-water bath The resulting solid was filtered off to wash the solid to wash the solid again The solid was extracted with refluxing ethanol The ethanol solution was dried