Hydrochloric Acid → 4-(4-Methoxyphenoxy)biphenyl

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	N,N-Dimethylglycine	HCID 673	—
Reactant	4-Bromobiphenyl	HCID 7101	—
Reactant	4-Methoxyphenol	HCID 9015	—
Reactant	Cesium carbonate	HCID 10796	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-(4-Methoxyphenoxy)biphenyl	HCID 266864	132.3%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of 4-methoxyphenol (3.99 g, 32.17 mmol) and 4-bromobiphenyl (5 g, 21.45 mmol) in anhydrous dioxane (40 mL) were added cesium carbonate (13.98 g, 42.9 mmol) and N,N-dimethylglycine.HCl (0.898 g, 6.4 mmol). The reaction mixture was flushed with nitrogen. Copper (I) iodide (0.408 g, 2.145 mmol) was added and the reaction mixture was stirred at 90° C. for 18 h under an atmosphere of nitrogen. The mixture was diluted with water (100 mL) and extracted with EtOAc (250 mL). Aqueous layer was re-extracted with EtOAc (150 mls). The organic layers were combined, dried over anhydrous Na2SO4, and concentrated to obtain the title product 7.84 g.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07402684B2
Source dataset	uspto-grants-2008_07
ORD ID	ord-911a70802ff449069dc709acb0634781
Source note	uspto-grants-2008_07