Triethylamine → HCID 50997079, compound

Temperature

0 °C

3-Cyclopropyl-2,2-difluoro-1-propanol (48.0 g 0.35 mol, 1 eq), prepared as in Example 4, was added to a 1 L jacketed vessel equipped with a mechanical stirrer, thermometer and gas inlet adapter. Dichloromethane (480 mL) and then triethylamine (42.7 g, 0.421 mol, 1.2 eq) was added. The reaction mixture was cooled to 0° C. and then perfluorobutane sulfonyl fluoride (127.9 g, 0.421 mol, 1 eq) was slowly added drop wise over 30 minutes maintaining a temperature of less than 5° C. The reaction was shown to be complete after one hour by thin layer chromatography (1:1/ethyl acetate:hexanes, silica, KMnO4 dip). The mixture was concentrated under vacuum at 30° C. to provide a brown oil. Water (150 mL) was added and the product was extracted with methyl tert-butylether (250 mL). The organic layer was washed with water (2×150 mL), dried with anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to provide 3-cyclopropyl-2,2-difluoropropyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (140 g, 95% yield) as a brown oil. GC/MS: consistent with mass.

1. additionwas added to a 1 L
2. customequipped with a mechanical stirrer
3. customwise over 30 minutes
4. temperaturemaintaining a temperature of less than 5° C
5. concentrationThe mixture was concentrated under vacuum at 30° C.
6. customto provide a brown oil
7. extractionthe product was extracted with methyl tert-butylether (250 mL)
8. washThe organic layer was washed with water (2×150 mL)
9. dry with materialdried with anhydrous magnesium sulfate
10. filtrationfiltered
11. customThe filtrate was evaporated under reduced pressure

ORD record

ord-df30df0fd3fb4328b0e18344e08d6125

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324417B2