Dimethyl(3,3,4,4,5,5,6,6,6-nonafluorohexyl)chlorosilane → HCID 86663261, compound

Temperature

60 °C

In an oven-dried 250-mL round bottom flask, 3,3,4,4,5,5,6,6,6-nonafluorohexyldimethylchlorosilane (4.58 g, 13.4 mmol) was dissolved in anhydrous THF (10 mL) and cooled in an ice bath. Ethynylmagnesium bromide (34 mL, 17 mmol, 0.5 M in THF) was added slowly, then the mixture was heated to 60° C. for 12 hr. The reaction was quenched with water and dilute sulfuric acid (i.e., a 10 wt % solution of the sulfuric acid (95-98%) in water) to dissolve the salts, then hexane was added and the organic layer was separated. The organic layer was washed with water (5×20 mL), dried over magnesium sulfate, filtered, and concentrated under vacuum to yield the crude product. Purification using chromatography on silica gel with hexane as an eluant yielded a colorless liquid (3.52 g, 10.6 mmol, 80%). 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. temperaturecooled in an ice bath
2. customThe reaction was quenched with water and dilute sulfuric acid (i.e.
3. dissolutiona 10 wt % solution of the sulfuric acid (95-98%) in water) to dissolve the salts
4. additionhexane was added
5. customthe organic layer was separated
6. washThe organic layer was washed with water (5×20 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. customto yield the crude product
11. customPurification

ORD record

ord-e956c88b9c7444ada11a418472e5f23b

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08920679B2