Cesium carbonate → 2-Chloro-N-(5-fluoro-2-methoxyphenyl)-4-(methylsulfonyl)aniline

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Benzenamine, 2-chloro-4-(methylsulfonyl)-	HCID 25801	—
Reactant	2-Bromo-4-fluoroanisole	HCID 136292	—
Reactant	Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphine	HCID 21081571	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Chloro-N-(5-fluoro-2-methoxyphenyl)-4-(methylsulfonyl)aniline	HCID 66995723	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 2-bromo-4-fluoroanisole (6.0 g), 2-chloro-4-methylsulphonylaniline (9.0 g), cesium carbonate (14.7 g), palladium acetate (0.33 g) and 2-(dicyclohexylphosphino)-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (0.54 g) in dioxane (60 ml) was heated at 100° C. for 20 h. The mixture was cooled, and partitioned between ethylacetate/water. The organics were separated, washed with brine, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 25% ethylacetate/isohexane. Yield 3.2 g

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08003703B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-4ad07167b03043e1a76f357c5224636f
Source note	uspto-grants-2011_08