1,10-Phenanthroline → HCID 12089253, compound

Participants

Reaction Steps

A solution of 6.79 g (24 mmol) of 4-bromoiodobenzene in 100 mL of diethyl ether was cooled to −70° C., added with 14 mL (23.4 mmol) of n-butyllithium dropwise, and stirred for 30 min and further for 30 min after elevating the temperature to 0° C. The resulting solution was added dropwise to 100 mL of a diethyl ether solution of 3.60 g (20 mmol) of 1,10-phenanthroline at 0° C., and the mixture was stirred for 3 h. Ice water was added, an organic layer was separated, and an aqueous layer was extracted with dichloromethane (100 mL×2). The obtained organic layers were combined and dried over anhydrous sodium sulfate, followed by filtration. To a filtrate, 20 g of manganese dioxide was added, and the mixture was stirred for 30 min. Thereafter, 20 g of manganese dioxide was further added, and the mixture was stirred for one hour and allowed to stand at room temperature overnight. The reaction solution was filtered, and a filtrate was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain 2.50 g (yield: 37%) of 2-(4′-bromophenyl)-1,10-phenanthroline as a yellow solid.

Provenance & Evidence