Potassium Carbonate → 4'-Chloro-2-methyl-[1,1'-biphenyl]-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Bromo-3-methylaniline	HCID 23359	—
Reactant	4-Chlorophenylboronic acid	HCID 74299	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4'-Chloro-2-methyl-[1,1'-biphenyl]-4-amine	HCID 60039188	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

4-bromo-3-methylaniline (5.1 g, 27.4 mmol), 4-chlorophenylboronic acid (5.1 g, 32.9 mmol), Pd(dppf)Cl2 (1.1 g, 1.4 mmol), and 2M aqueous K2CO3 (27.4 mL, 54.8 mmol) were dissolved in 1,4-dioxane (110 mL) and the resulting mixture was heated to 100° C. After 2 h 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-68c8751463744f90910a9e1d1a9206fe
Source note	uspto-grants-2014_06