Phosphate → 1-(Cyclopentylthio)-3-iodo-5-methylbenzene

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Reaction Steps

A mixture of 1,3-diiodo-5-methylbenzene (2.00 g), tris(dibenzylideneacetone)dipalladium (0) (20 mg), bis(diphenylphosphino)ferrocene (22 mg), triethylamine (1.5 ml) and 1-methyl-2-pyrrolidinone (3 ml) were stirred at to 20° under nitrogen for 1 h. Cyclopentanethiol (0.15 ml) was added and the mixture was heated to 60° for 18 h. The mixtue was cooled to 20° and was treated with phosphate buffer solution (pH 6.5) and water. The mixture was extracted with EtOAc and the extract dried (Na2SO4). Solvent evaporation in vacuo gave a residue which was purified by Flashmaster™ chromatography (silica, 70 g). Elution with cyclohexane gave the title compound (444 mg). LCMS RT=4.21 min.

Provenance & Evidence