Two new ways to P2P, starting with bromobenzene
[Bull Soc Chem Jap 57, 242 (1984)]
To a stirred solution of an aryl bromide (60 mmol), isopropenyl acetate (9g, 90 mmol) and dichlorobis(tri-o-tolylphosphine)palladium (0.47g, 0.67 mmol) in dry toluene (30 ml), under nitrogen, was added tributyltin methoxide (25.9 ml, 90 mmol; Aldrich). The mixture was stirred and heated at 100 deg C for 5 hr, cooled and the solvent evaporated in vacuo. The residue was chromatographed on silica gel, to afford the aryl-2-propanone in 67% yield.
[Chem Lett 597 (1982)]
To a stirred solution of an aryl bromide (53.9 g, 200 mmol) in DMF (1 liter) was added cuprous iodide (32.4 g, 167 mmol) and potassium acetylacetonate hemihydrate (125g, 834 mmol; Aldrich). The mixture was stirred and heated at 100 deg C for 24 hr, cooled, stirred with 2M sodium hydroxide (250 ml) for 1 hr and extracted with toluene (2x500 ml). The combined extracts were washed with water, 1M hydrochloric acid and satd. aq. sodium bicarbonate, dried over magnesium sulphate and concentrated in vacuo to leave a dark brown oil, which after purification gave the aryl-2-propanone in 65% yield.