Triphenylphosphine → 3,3',5,5'-Tetramethyl-7,7'-bis[3,5-bis(trimethylsilylethynyl)phenyl]-1,1'-biadamantane

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Reaction Conditions

Reaction Steps

Next, 50 g (62.9 mmol) of the previously obtained 3,3′,5,5′-tetramethyl-7,7′-bis(3,5-dibromophenyl)-1,1′-biadamantane, 3.53 g (5.0 mmol) of dichlorobistriphenylphosphinepalladium, 6.60 g (25.2 mmol) of triphenylphosphine, 4.79 g (25.2 mmol) of copper(II) iodide and 750 ml of triethylamine were added to a flask and stirred. The mixture was raised to 75° C., and then 37.1 g (377.7 mmol) of trimethylsilylacetylene was slowly added. After stirring at 75° C. for 7 hours, the temperature was raised to 120° C. to remove the triethylamine. After returning to room temperature, 1000 ml of dichloromethane was added to the reaction mixture and stirring was continued for 20 minutes. The precipitate was removed by filtration, and 1000 ml of a 5% hydrochloric acid aqueous solution was added to the filtrate for liquid separation. The organic layer was washed three times with 1000 ml of water, and then the solvent of the organic layer was removed under reduced pressure. The obtained compound was dissolved in 1500 ml of hexane. The insoluble portion was removed by filtration and the hexane in the filtrate was removed under reduced pressure. After introducing 1000 ml of acetone thereinto, the precipitate was washed 3 times with acetone to obtain 43 g of 3,3′,5,5′-tetramethyl-7,7′-bis[3,5-bis(trimethylsilylethynyl)phenyl]-1,1′-biadamantane.

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