1,10-Phenanthroline → 2-(3-Bromophenyl)benzoxazole

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Bromoaniline	HCID 11992	—
Reactant	Benzoyl chloride, 3-bromo-	HCID 74377	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-(3-Bromophenyl)benzoxazole	HCID 870520	76.3%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of 3-bromobenzoyl chloride (10.0 g, 45.6 mmol), 2-bromoaniline (7.91 g, 46 mmol), Cs2CO3 (30 g, 92 mmol), CuI (0.437 g, 2.3 mmol) and 1,10-phenanthroline (0.829 g, 4.6 mmol) in anhydrous 1,4-dioxane (110 ml) was heated at 120° C. for 8 h. After cooling to RT, the mixture was poured into ethyl acetate (300 ml), worked up with water (250 ml). The aqueous solution was extracted with dichloromethane (300 ml). The organic phase was collected, combined, and dried over Na2SO4. Purification by a short silica gel column (hexanes/ethyl acetate 3:1) gave a solid which was washed with hexanes to give a light yellow solid 1 (9.54 g, 76% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09051284B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-716d9ebe65074cc0a5264433d5991cdb
Source note	uspto-grants-2015_06