4-Bromoanisole → (E)-3-Cyclohexyl-2-(4-methoxy-phenyl)-prop-2-en-1-ol

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Reaction Steps

Following the method of example 46a, Suzuki coupling of 1-bromo-4-methoxy-benzene (0.65 g, 3.48 mmol) with (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl) -prop-2-en-1-ol (1.05 g, 3.94 mmol) in the presence of tetrakis(triphenylphosphino)palladium(0) (0.25 g, 0.22 mmol) and cesium fluoride (1.69 g, 11 mmol) in dioxane (20 mL) gives the title compound (0.5 g). 1H-NMR (CDCl3) δ=0.92-2.15 (m, 10H), 2.62-2.77 (m, 1H), 3.82 (s, 3H), 4.23-4.29 (m, 2H), 6.02-6.11 (m, 1H), 6.86-6.94 (m, 2H), 7.11-7.17 (m, 2H).

Provenance & Evidence