Water → HCID 86708721, compound

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of 2,7-dibromo-9,10-dihydrophenanthrene (3.5 g, 10.35 mmol), tributyl-(1-ethoxyvinyl)tin (3.8 mL, 11.4 mmol), tetrakis(triphenylphosphine)palladium(0) (598 mg, 0.52 mmol) and dichloro[1,1-bis(diphenyl-phosphino)ferrocene]palladium(II) (378 mg, 0.52 mmol) in 1,4-dioxane (1.0 mL) was heated to 85° C. for 18 hours, cooled to room temperature and N-bromosuccinimide (2.21 g, 12.42 mmol) and water (25 mL) were added. The reaction mixture was stirred at room temperature for 2 hours, diluted with ethyl acetate. The organics were washed with water and brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography to yield 2-bromo-1-(7-bromo-9,10-dihydrophenanthren-2-yl)ethanone (635 mg, 16%).

Provenance & Evidence