Sodium Carbonate → (E)-3-Cyclohexyl-2-(4-isopropylsulfanyl-phenyl)-acrylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Add potassium acetate (2.5 g, 26 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (2.42 g, 9.52 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (629 mg, 0.86 mmol) to a solution of 1-bromo-4-isopropylsulfanyl-benzene (2.0 g, 8.65 mmol) in 30 mL DMF and stir 2 hour at 80° C. Then add (Z)-2-bromo-3-cyclohexyl-acrylic acid ethyl ester is (4.5 g, 17.3 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (629 mg, 0.86 mmol) and sodium carbonate solution (2 M, 21.0 mL, 42.0 mmol) and stir at 80° C. over night. Add 100 mL ethyl acetate and filter. Wash with water and brine, filter through a hydrophobic filter paper and concentrate. Further purification via silica gel column chromatography, eluting with a gradient from 100:0 to 98:2 hexane:ethyl acetate affords the title compound as yellow oil (1.25 g). MS (m/e): 333 (M+H).

Provenance & Evidence