Cesium carbonate → 2-Fluoro-3-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic Acid Methyl Ester

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Pyrrolidone	HCID 12025	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Methyl 3-bromo-2-fluoro-5-(trifluoromethyl)benzoate	HCID 69361010	—
Reactant	3-Chloro-2-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic acid methyl ester	HCID 69589922	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Fluoro-3-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic Acid Methyl Ester	HCID 69589685	—

Reaction Steps

3-Bromo-2-fluoro-5-trifluoromethylbenzoic acid methyl ester (500 mg, 1.95 mmol)), caesium carbonate (950 mg, 2.92 mmol), pyrrolidin-2-one (248 mg, 2.92 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (68 mg, 0.117 mmol) and tris(dibenzylideneacetone)dipalladium (0) (36 mg, 0.039 mmol) were refluxed under argon in dioxane (7 ml) for 18 h. After cooling, the mixture was filtered and evaporated in vacuo. Column chromatography on silica gel eluting with a gradient of 20–50% ethyl acetate in hexane gave a mixture of D24 and 3-chloro-2-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic acid methyl ester (195 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06992103B2
Source dataset	uspto-grants-2006_01
ORD ID	ord-1062ebf2599f40babd596cc640ecafcd
Source note	uspto-grants-2006_01