4-Iodoaniline → 2',4'-Dichloro-[1,1'-biphenyl]-4-amine

Participants

Role	Name	HCID	Charge
Reactant	4-Iodoaniline	HCID 10893	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(2,4-Dichlorophenyl)boronic acid	HCID 2734659	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2',4'-Dichloro-[1,1'-biphenyl]-4-amine	HCID 9964725	—

Reaction Conditions

Temperature	70 °C

Reaction Steps

4-Iodoaniline (6.9 g, 31.7 mmol), (2,4-dichlorophenyl)boronic acid (7.3 g, 38.0 mmol), Pd(dppf)Cl2 (1.3 g, 1.6 mmol), and 2M aqueous K2CO3 (31.7, 63.4 mmol) were dissolved in 1,4-dioxane (127 mL) and the resulting mixture was heated to 70° C. After 2.5 d the resulting mixture was cooled to room temperature, concentrated, diluted with EtOAc and 4M aqueous NaCl, and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organics were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748624B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-70f8c933c2d54f4198c7ae1695175cad
Source note	uspto-grants-2014_06