1-Butanesulfonamide, 1,1,2,2,3,3,4,4,4-nonafluoro-N-(2-hydroxyethyl)-N-methyl-

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

Procedure: A 500 mL three-necked round bottom flask was charged with 16.86 g of C4F9SO2N(CH3)CH2CH2OH (MW=357; 47.22 mmol; Example 2, A from WO 01/30873), 4.35 g HSCH2CO2H (MW=92.12, 47.22 mmol; available from Sigma-Aldrich), 2 drops of CF3SO3H catalyst, and 120 mL toluene. The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours. Water was removed by azeotropic distillation. Fourier Transform Infrared Spectroscopy (FTIR) analysis indicated the formation of ester. Toluene was stripped using a rotary evaporator (21.35 g solid). The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours Water was removed by azeotropic distillation a rotary evaporator (21.35 g solid)

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

Procedure: A 500 mL three-necked round bottom flask was charged with 16.86 g of C4F9SO2N(CH3)CH2CH2OH (MW=357; 47.22 mmol; Example 2, A from WO 01/30873), 4.35 g HSCH2CO2H (MW=92.12, 47.22 mmol; available from Sigma-Aldrich), 2 drops of CF3SO3H catalyst, and 120 mL toluene. The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours. Water was removed by azeotropic distillation. Fourier Transform Infrared Spectroscopy (FTIR) analysis indicated the formation of ester. Toluene was stripped using a rotary evaporator (21.35 g solid). The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours Water was removed by azeotropic distillation a rotary evaporator (21.35 g solid)

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

Procedure: A 500 mL three-necked round bottom flask was charged with 16.86 g of C4F9SO2N(CH3)CH2CH2OH (MW=357; 47.22 mmol; Example 2, A from WO 01/30873), 4.35 g HSCH2CO2H (MW=92.12, 47.22 mmol; available from Sigma-Aldrich), 2 drops of CF3SO3H catalyst, and 120 mL toluene. The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours. Water was removed by azeotropic distillation. Fourier Transform Infrared Spectroscopy (FTIR) analysis indicated the formation of ester. Toluene was stripped using a rotary evaporator (21.35 g solid). The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours Water was removed by azeotropic distillation a rotary evaporator (21.35 g solid)

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

Procedure: CF3(CF2)3SO2N(Me)CH2CH2I was made as follows: CF3(CF2)3SO2N(Me)CH2CH2OH was reacted with an excess of thionyl chloride in methylene chloride at 25-45° C. to give CF3(CF2)3SO2N(Me)CH2CH2Cl, which (7.1 g) was mixed with a solution of 6.0 g NaI in acetone. The resulting solution was stirred at reflux, and the conversion to CF3(CF2)3SO2N(Me)CH2CH2I was followed by GC. At 24 hours, conversion was 14 percent, and 6.0 g more NaI was added; at 3 days, conversion was 46 percent; at 6 days, conversion was 72 percent, and 6.0 g NaI was added; at 13 days, 96 percent conversion was achieved. The resulting product was precipitated with water and recrystallized from hexane to provide 6.2 g white plates with a m.p. of 80-82° C. FO2S(CF2)2O(CF2)2I was obtained from Sigma-Aldrich Chemical Company, St. Louis, Mo. C3F6O(isoC3F3O)5CF(CF3) can be prepared essentially as described by Chen et. al. in J Fluorine Chem. 65, 59 (1993). I(CF2)4I was obtained from Sigma-Aldrich Chemical Company, St. Louis, Mo. CF3(CF2)7Br was obtained from 3M Company, St. Paul, Minn., and is available from Sigma-Aldrich Chemical Company, St. Louis, Mo. Sodium acetate was obtained from Sigma-Aldrich Chemical Company, St. Louis, Mo. Dimethylsulfoxide (DMSO) was obtained from Alfa Aesar, Ward Hill, Mass. Tetrahydrofuran (THF) was obtained from EMD Chemicals, Inc., Gibbstown, N.J. p-Toluenesulfonic acid was obtained from J. T. Baker, Phillipsburg, N.J. NaHCO3 was obtained from EMD Chemicals, Inc., Gibbstown, N.J.

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

Procedure: A 500 mL three-necked round bottom flask was charged with 16.86 g of C4F9SO2N(CH3)CH2CH2OH (MW=357; 47.22 mmol; Example 2, A from WO 01/30873), 4.35 g HSCH2CO2H (MW=92.12, 47.22 mmol; available from Sigma-Aldrich), 2 drops of CF3SO3H catalyst, and 120 mL toluene. The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours. Water was removed by azeotropic distillation. Fourier Transform Infrared Spectroscopy (FTIR) analysis indicated the formation of ester. Toluene was stripped using a rotary evaporator (21.35 g solid). The mixture was heated to reflux under nitrogen at 115–120° C. with a mechanical stirrer for 8 hours Water was removed by azeotropic distillation a rotary evaporator (21.35 g solid)