Hydrogen Peroxide → 2-Iodo-4'-methyl-1,1'-biphenyl

Participants

Reaction Steps

A mixture of 1,2-diiodobenzene (6.6 g) and tetrakis(triphenylphosphine)palladium(0) (0.34 g) in AR toluene (100 ml) was stirred under a nitrogen atmosphere at ambient temperature. A solution of sodium carbonate (2 g) in water (15 ml) was added. The resulting orange mixture was stirred and heated under reflux while a solution of 4-methylbenzeneboronic acid (1.36 g) in industrial methylated spirit (40 ml) was added dropwise over a period of 40 minutes. The mixture obtained was heated under reflux for an additional 4 hours, then cooled to ambient temperature. Aqueous hydrogen peroxide (30%; 1 ml) was added and the resulting mixture was stirred for 1 hour at ambient temperature. Saturated aqueous sodium chloride solution (50 ml) was then added and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases were washed with saturated aqueous sodium chloride solution (1×70 ml), dried over magnesium sulphate and evaporated to give an orange oil. This oil was triturated with petroleum ether (b.p. 40°-60° C.) (200 ml) to give a gum which was partially purified by flash chromatography on silica gel (eluting with petroleum ether (b.p. 40°-60° C.): ethyl acetate (4:1)) then further purified by high performance liquid chromatography on a silica column (eluting with petroleum ether (b.p. 60°-80° C.) at 200 ml/minute), to give the intermediate compound 2'-iodo-4-methylbiphenyl as a colourless oil (1.3 g).

Provenance & Evidence