Sodium Carbonate → 2,2,2-Trifluoro-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Bromo-5-fluoropyridine	HCID 2783171	—
Reactant	2,2,2-Trifluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethan-1-one	HCID 56973060	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2,2,2-Trifluoro-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone	HCID 59161928	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

Pd(dppf)Cl2 (2.5 g, 3.3 mmol) was added to a degassed, ambient temperature solution of 2,2,2-trifluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (20 g, 67 mmol), 2-bromo-5-fluoropyridine (11.6 g, 67 mmol) and sodium carbonate (12.7 g, 134 mmol) in N,N-dimethylformamide (4400 mL) and water (90 mL). After heating at 90° C. overnight, the reaction mixture was poured into ice (400 g) and extracted with diethyl ether. The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with petroleum ether/ethyl acetate (20:1) afforded the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08193228B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-b30d3b8e4fcc46e4a25fd3fdda072028
Source note	uspto-grants-2012_06