Sodium Carbonate → (E)-3-Cyclohexyl-2-(4-methanesulfonyl-3-trifluoromethoxy-phenyl)-prop-2-en-1-ol

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Reaction Steps

Heat a suspension of 4-bromo-1-methanesulfonyl-2-trifluoromethoxy-benzene (0.71 g, 2.23 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (0.77 g, 2.91 mmol), 2 M aqueous sodium carbonate solution (2.2 mL, 4.4 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (164 mg, 2.13 mmol) in 5.7 mL DMF to 80° C. for 2 h. Dilute the mixture with ethyl acetate, separate the organic layer, wash it with water followed by saturated sodium chloride solution. Filter through a hydrophobic filter paper and remove the solvent under vacuum. Further purify the resulting residue by column chromatography, eluting with a gradient from 100:0 to 30:70 hexanes:ethyl acetate to afford the title compound (0.75 g) as a yellow oil. MS (m/e): 396 (M+4H2O).

Provenance & Evidence