Triphenylphosphine → 2-methyl-4-(2,5-dimethylphenyl)-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

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Reaction Steps

A mixture containing 30.0 g (107.5 mmol)) of 4-bromo-2-methyl-3,5,6,7-tetrahydro-2H-s-indacen-1-one, 410 ml of dimethoxyethane, 21.0 g (135.8 mmol) of 2,5-dimethylphenyl boronic acid, 20.0 g (321 mmol) of potassium hydroxide and 72 ml of water was degassed and the flask atmosphere replaced with nitrogen. Stirring was initiated and 0.60 g (2.7 mmol) of palladium acetate and 2.4 g (9.1 mmol) of triphenylphosphine were added. The reaction mixture was stirred at 78° C. for 4 h. After cooling, the mixture was poured into water and the organic phase was separated. The aqueous phase was extracted two times with 200 ml of dichloromethane. The combined organic fractions were dried and solvents removed on a rotoevaporator giving 45 g of crude product. The crude product was dissolved in dichloromethane and filtered through a plug of silica gel to give 24 g of target compound as an oil after evaporation of the solvent (77% yield based on the indacen-1-one starting material).

Provenance & Evidence