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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
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	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2',4'-Dichloro-[1,1'-biphenyl]-4-amine	HCID 9964725	—

Reaction Steps

4-Iodoaniline (10.0 g, 45.7 mmol), (2,4-dichlorophenyl)boronic acid (10.5 g, 54.8 mmol), Pd(dppf)Cl2 (3.7 g, 4.6 mmol), and K2CO3 (12.6 g, 91.3 mmol) were dissolved in 1,4-dioxane (200 mL) and water (50 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045389B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-108c6e3e01c5424b9dd093598390523a
Source note	uspto-grants-2015_06