Vinyltrimethylsilane → 4-Bromo-2-methyl-1-vinylbenzene

참여 물질

반응 단계

KF (870 mg, 15 mmol), n-Bu4NCl (2.77 g, 10 mmol), Pd(dba)2 (145 mg, 0.25 mmol), molecular sieves (4 Ang, 200 mg, activated balls), 5-bromo-2-iodo-1-methylbenzene (1.49 g, 5 mmol), trimethyl(vinyl)silane (2.7 mL, 20 mmol), and toluene (10 mL) were added to a pressure vessel and sparged with Ar. The vial was sealed and microwaved at 170° C. for 30 min. The mixture was cooled to ambient temperature, diluted with hexanes, filtered and concentrated. The crude oil was purified by flash chromatography (100% hexanes) to yield 30A (750 mg, 76%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.31 (s, 3 H) 5.31 (dd, J=10.99, 1.10 Hz, 1 H) 5.62 (dd, J=17.59, 1.10 Hz, 1 H) 6.84 (dd, J=17.04, 10.99 Hz, 1 H) 7.26-7.35 (m, 3 H).

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