1,10-Phenanthroline → HCID 12089253, compound

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.

1. customto 0° C
2. stirringthe mixture was stirred for 3 h
3. customan organic layer was separated
4. extractionan aqueous layer was extracted with dichloromethane (100 mL×2)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfollowed by filtration
7. additionTo a filtrate, 20 g of manganese dioxide was added
8. stirringthe mixture was stirred for 30 min
9. additionThereafter, 20 g of manganese dioxide was further added
10. stirringthe mixture was stirred for one hour
11. waitto stand at room temperature overnight
12. filtrationThe reaction solution was filtered
13. concentrationa filtrate was concentrated under reduced pressure
14. custompurified by silica gel column chromatography

ORD record

ord-c7a8132d3e8e4df88427f86b6cb2cf85

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273002B2