Sodium Carbonate → {[(2,3-Dichloro-5-ethenylphenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane

関与物質

反応条件

反応手順

{[(5-Bromo-2,3-dichlorophenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane (1 eq.) from the previous step and 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.) were combined in a 2:1 (v/v) mixture of DMF:n-PrOH (0.11 M). To this solution was then added palladium(II) acetate (0.05 eq.) and triphenylphosphine (0.15 eq.) before the vessel was repeatedly evacuated and back-filled with nitrogen. Finally, 2 N aq. Na2CO3 (2 eq.) was added and the resulting biphasic suspension was heated at 90° C. for 8 h. The now black suspension was cooled to RT, diluted with water and extracted with 1:1 (v/v) hexanes:ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a black oil.

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