1,10-Phenanthroline → 1,3-bis(1H-benzo[d]imidazol-1-yl)benzene

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Benzimidazole	HCID 5798	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Benzene, 1,3-diiodo-	HCID 12270	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Methanol	HCID 887	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	1,3-bis(1H-benzo[d]imidazol-1-yl)benzene	HCID 57182155	127.5%

Reaction Steps

In a 1 L round-bottomed flask 1,3-diiodobenzene (26.43 g, 80 mmol), 1H-benzo[d]imidazole (20.82 g, 176 mmol), and 1,10-phenanthroline (5.77 g, 32.0 mmol), CuI (3.05 g, 16 mmol), and cesium carbonate (120 g, 369 mmol) were combined in anhydrous DMF (350 mL) to give a brown suspension. The reaction was purged with N2 for 20 minutes and then heated to reflux for 24 hours. The reaction mixture was passed thought a plug of silica gel (5% MeOH in DCM) to obtain the crude product. The crude product was subjected to silica gel chromatography (SiO2, 400 g, 2% MeOH to 5% MeOH in DCM) to ultimately obtain the final product (12.66 g, 51%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08563737B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-0e0d1f61ce474fedacb57dd3be9fdb32
Source note	uspto-grants-2013_10