Allyl bromide → HCID 11433681, compound

Temperature

60 °C

In an oven-dried round-bottom flask equipped with a stir bar and cooled under N2, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyldiisopropylsilane (9.97 g, 17.7 mmol) was dissolved in 15 mL anhydrous benzene (benzene dried by boiling off 10% by volume prior to use). To this was added allyl bromide (3.22 g, 26.6 mmol, 1.5 eq.) and PdCl2 (35 mg, 1 mol %). The solution was heated to 60° C. for 15 hr, then cooled, and concentrated via rotary evaporation. The resulting suspension was dissolved in pentane, filtered to remove residual catalyst, and then solvent was removed to yield (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyldiisopropylsilyl)bromide (11.3 g) as a pale brown liquid. The bromide was treated under anhydrous conditions with 1.2 eq. (based on initial silane) of ethynylmagnesium bromide and heated to 40° C. for 6 hr. The reaction was quenched with water and dilute sulfuric acid, pentane was added, and the organic layer was separated. The organic layer was washed with water (6×50 mL), dried over MgSO4, filtered, and concentrated via rotary evaporation. Further purification via flash chromatography using hexane yielded pure (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyldiisopropylsilyl)acetylene (9.0 g, 15 mmol, 87%) as a colorless liquid. Analysis of the product provided the following data: 1H-NMR (200 MHz, CDCl3) δ=2.4 (s, 1H), 2.2 (m, 2H), 1.0 (m, 14H), 0.8 (m, 2H).

1. customIn an oven-dried round-bottom flask equipped with a stir bar
2. temperaturecooled under N2
3. customdried
4. temperaturecooled
5. concentrationconcentrated via rotary evaporation
6. dissolutionThe resulting suspension was dissolved in pentane
7. filtrationfiltered
8. customto remove residual catalyst
9. customsolvent was removed

ORD record

ord-0e84415a49464ccfa83b0814b416395e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08920679B2