Potassium Carbonate → (E)-3-cyclohexyl-2-(3-fluoro-4-methanesulfonyl-phenyl)-prop-2-en-1-ol

Participants

Reaction Steps

Heat a mixture of 4-bromo-2-fluoro-l -methanesulfonyl-benzene (220 mg, 0.86 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (298 mg, 1.12 mmol), potassium carbonate (356 mg, 2.58 mmol) and tetrakis(triphenylphosphino)palladium(0) (99 mg, 86 μmol) in 40 mL toluene, 5 mL iso-propanol and 5 mL water to reflux for 2 h. After cooling to r.t. extract with ethyl acetate, wash the combined organic extracts with brine, dry them over sodium sulfate, filtrate and concentrate to obtain a brown oil. Purify the crude product by column chromatography, eluting with a gradient from 100:0 to 0:100 hexanes:ethyl acetate to obtain (E)-3-cyclohexyl-2-(3-fluoro-4-methanesulfonyl-phenyl)-prop-2-en-1-ol (238 mg) as a pale yellow oil. MS (m/e): 295 [(M−H2O)+H].

Provenance & Evidence