Sodium Carbonate → 2-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-Bromo-3-chloroaniline	HCID 88888	—
Reactant	4-(Trifluoromethyl)phenylboronic acid	HCID 2734389	—
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-Chloro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-amine	HCID 68834284	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

4-bromo-3-chloroaniline (2.1 g, 10.2 mmol), (4-(trifluoromethyl)phenyl)boronic acid (2.7 g, 14.2 mmol), Pd(dppf)Cl2 (744 mg, 1.0 mmol), 2M aqueous Na2CO3 (15.3 mL, 30.5 mmol) were dissolved in 1,4-dioxane (30 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, was diluted with EtOAc, washed with water and brine. The organic layer was dried (Na2SO4), concentrated and diethyl ether was added. The resulting precipitate was filtered and dried in vacuo 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-d72259e8bf7c48729e74a335ef3854e4
Source note	uspto-grants-2014_06