1,10-Phenanthroline → 1-Bromo-4-(cyclopentyloxy)benzene

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Cyclopentanol	HCID 7298	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Bromo-4-iodobenzene	HCID 11522	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Product	1-Bromo-4-(cyclopentyloxy)benzene	HCID 22599958	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a stirred mixture of 1-bromo-4-iodo-benzene, (1.00 g, 3.53 mmol), o-phenanthroline (255 mg, 1.41 mmol) and cyclopentanol (1.50 g, 17.44 mmol) in toluene (1.500 mL) was added copper(I) iodide (135.00 mg, 0.70 mmol) and Cs2CO3 (2.87 g, 8.83 mmol). The resulting mixture was then stirred at 120° C. in a sealed tube for 15 hours. The solvent was then removed under reduced pressure and the product was purified by flash chromatography (eluted by hexane).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08481733B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-2e6af75726804d49a308d65bbd65f981
Source note	uspto-grants-2013_07