1H,1H,2H,2H-Perfluorooctyldimethylchlorosilane → HCID 86663263, compound

Temperature

60 °C

In an oven-dried 250-mL round bottom flask, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyldimethylchlorosilane (9.67 g, 21.9 mmol) was dissolved in 20 mL anhydrous THF. Ethynylmagnesium bromide (50 mL, 25 mmol, 0.5 M in THF) was added and the mixture was heated to 60° C. for 12 hr. After allowing the mixture to cool to room temperature, the reaction was quenched by the dropwise addition of water, followed by the addition of dilute sulfuric acid to dissolve the magnesium salts. The organic layer was separated, washed with water (3×20 mL) and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product was purified by chromatography on silica gel using hexane as an eluant. Removal of solvent yielded 9.0 g (21 mmol, 96%) of the product as a colorless liquid. Analysis of the colorless product provided the following data: 1H-NMR (200 MHz, CDCl3) δ=2.4 (s, 1H), 2.1 (m, 2H), 0.8 (m, 2H), 0.2 (s, 6H).

1. temperatureto cool to room temperature
2. customthe reaction was quenched by the dropwise addition of water
3. additionfollowed by the addition of dilute sulfuric acid
4. dissolutionto dissolve the magnesium salts
5. customThe organic layer was separated
6. washwashed with water (3×20 mL) and brine
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. customThe crude product was purified by chromatography on silica gel
11. customRemoval of solvent

ORD record

ord-84dc760a22074a3cb7c86cf1c2fbcbc4

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08920679B2