4-Fluorophenol → 3-Bromo-4'-fluorodiphenyl ether

https://huagongshe.com/reaction/1909083

Participants

Role	Name	HCID	Charge
Reactant	4-Fluorophenol	HCID 9732	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Benzene, 1-bromo-3-iodo-	HCID 11561	—
Reactant	N,N-Dimethylglycine hydrochloride	HCID 75605	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	3-Bromo-4'-fluorodiphenyl ether	HCID 2778689	33.6%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of 1-bromo-3-iodo-benzene (1.00 g, 3.55 mmol), 4-fluorophenol (462 mg, 3.59 mmol), N,N-dimethylglycine hydrochloride (149 mg, 1.06 mmol), and cesium carbonate (2.28 g, 7.00 mmol) in DMA was added CuI (66.8 mg, 0.351 mmol). The reaction mixture was heated at 90° C. for 48 h, cooled to rt, and then poured into water and extracted with EtOAc (3×). The organic layers were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound as a colorless oil (319 mg, 32%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08598356B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-9f126d6ff2d241c58072265d5bde54d5
Source note	uspto-grants-2013_12