Allyl bromide → HCID 86594466, compound

Participants

Reaction Conditions

Reaction Steps

In an oven-dried round-bottom flask equipped with a stir bar and cooled under N2, 3,3,4,4,5,5,6,6,6-nonafluorohexyldiisopropylsilane (10.1 g, 27.8 mmol) was dissolved in allyl bromide (20 mL), and PdCl2 (50 mg) was added. 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 (3,3,4,4,5,5,6,6,6-nonafluorohexyldiisopropylsilyl)bromide (12.1 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 (3,3,4,4,5,5,6,6,6-nonafluorohexyldiisopropylsilyl)acetylene (9.90 g, 25.6 mmol, 92%) 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), 1.1 (m, 14H), 0.8 (m, 2H).

Provenance & Evidence