4-Iodoaniline → 4-(3,4-Difluorophenyl)aniline

Participants

Role	Name	HCID	Charge
Reactant	4-Iodoaniline	HCID 10893	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3,4-Difluorobenzeneboronic acid	HCID 2734337	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-(3,4-Difluorophenyl)aniline	HCID 61026287	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

4-Iodoaniline (800 mg, 3.7 mmol), (3,4-difluorophenyl)boronic acid (1.2 g, 7.3 mmol), Pd(dppf)Cl2 (267 mg, 0.4 mmol), and 2M aqueous K2CO3 (3.7 mL, 7.3 mmol) were dissolved in 1,4-dioxane (15 mL) and heated to 80° C. After 2 h the resulting mixture was cooled to room temperature and the layers were separated. The organic phase was 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-f8d2841087064ea984a5fa0bad3b90cb
Source note	uspto-grants-2014_06