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	1,4-Dioxane	HCID 31275	—
Solvent	Water ethylacetate	HCID 22728543	—
Product	4-(4-Methoxyphenoxy)biphenyl	HCID 266864	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of 4-bromobiphenyl (1.16 g, 5 mmol), 4-methoxyphenol (413 mg, 3.33 mmol), Cs2CO3 (2.17 g, 6.66 mmol) in anhydrous dioxane (10 mL) was purged with nitrogen for 10 min. Then copper (I) iodide (18 mg, .096 mmol) and N,N-dimethylglycine.HCl (41 mg, 0.29 mmol) were added. Reaction was stirred at 90° C. over night. Reaction mixture was cooled and poured over 1:1 mixture of EtOAc/water. Organic layer was separated, washed with water, brine, dried over anhydrous MgSO4 and concentrated to give the crude product. It was used in next step without purification (1.26 g, 91%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07576102B2
Source dataset	uspto-grants-2009_08
ORD ID	ord-49455cdf3db14f26a551dd54ca78ff20
Source note	uspto-grants-2009_08