3-(2-Chlorophenyl)-2-methylprop-1-ene synthesis

Yield:90794-46-0 61%

Reaction Conditions:

with palladium diacetate;caesium carbonate;4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 100; for 12 h;Suzuki-Miyaura Coupling;Temperature;Time;

Steps:

Synthesis of Methylallyl Alkenes

General procedure: A solution of 2-methyl-2-propen-1-ol (5 mL), boronic acid (4.1 mmol, 1 equiv.), palladium(II) acetate (3.8 mg, 0.017 mmol, 0.0041 equiv.), Xantphos (38 mg, 0.068 mmol, 0.0167 equiv.) and cesium carbonate (2.3 g, 7 mmol, 1.7 equiv.) was stirred in a sealed vial for 1.5 h at 140 °C, under microwave irradiation (reaction conditions a) or for 1 h at 120 °C, under microwave irradiation (reaction conditions b) or for 12 h at 100 °C, under classical heating (reaction conditions c). Then the solid residue was fitered off. The filtrate was puried by fractional distillation under atmospheric pressure on a Vigreux column (rst fraction: 2-methyl-2-propen-1-ol, b.p. 115 °C, second fraction: alkene with reported b.p.) to obtain desired alkene. 1-Chloro-2-(2-methylallyl)benzene (1): obtained from (2-chlorophenyl)boronic acid (641 mg) using 1 method c, as a colorless oil (420 mg, 61%), b.p. 190 °C. H-NMR (CDCl , 200 MHz): δ = 7.49-7.09 3 13 (m, 4H, 4 Ar-H), 4.62 (s, 1H, CH ), 4.86 (s, 1H, CH ), 3.47 (s, 2H, CH ), 1.77 (s, 3H, CH ). C-NMR 2 2 2 3 (CDCl , 75 MHz): δ = 143.5 (C), 137.4 (C), 134.5 (C), 131.0 (CH), 129.5 (CH), 127.6 (CH), 126.7 3 + (CH), 112.3 (CH ), 41.4 (CH ), 22.5 (CH ). HRMS (ESI +) m/z calcd for C10H11Cl[M]+ : 166.0549. 2 2 3 10 11 Found: 166.0585.

References:

Tabélé, Clémence;Curti, Christophe;Kabri, Youssef;Primas, Nicolas;Vanelle, Patrice [Molecules,2015,vol. 20,# 12,p. 22890 - 22899]