Water → 2-[4',7'-Diphenylspiro(fluorene-9,2'-inden)-2-yl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

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Reaction Steps

n-BuLi (1.2 equiv) is added to a solution of 2-bromo-4′,7′-diphenylspiro(fluorene-9,2′-indene) (6b) in anhydrous THF at −78° C. After stirring the mixture for 1 h, 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.5 equiv) is added. The reaction mixture is allowed to warm to room temperature and then is stirred overnight. The reaction mixture is mixed with a large amount of water for extraction with ether. The organic extracts are washed with brine before drying over anhydrous MgSO4. The crude product of 2-[4′,7′-diphenylspiro(fluorene-9,2′-inden)-2-yl]-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (7b) is purified by column chromatography on silica gel using methylene chloride as the eluent yielding a white powder (79%).

Provenance & Evidence