1-Bromo-4-iodobenzene → (E)-2-(4-bromo-phenyl)-3-cyclopentyl-prop-2-en-1-ol

Participants

Reaction Conditions

Reaction Steps

According to the procedure described for example 26b the use of 4-bromo-1-iodo-benzene (1.42 g, 5.0 mmol), (E)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.01 g, 4.00 mmol), caesium fluoride (2.28 g, 15.0 mmol) and tetrakis(triphenylphosphino)palladium(0) (577 mg, 500 μmol) in 120 mL THF with heating to 60° C. for 16 h gives a brown oil. Purify the crude product by column chromatography, eluting with a gradient from 100:0 to 60:40 hexanes:ethyl acetate to obtain (E)-2-(4-bromo-phenyl)-3-cyclopentyl-prop-2-en-1-ol (446 mg) as a yellow oil. MS (m/e): 263 {[(79Br)M−H2O]+H}, 265 {[(81Br)M−H2O]+H}.

Provenance & Evidence