Ammonia → 3,5-Dibromo-2-(trifluoromethyl)pyridine

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	Potassium Fluoride	HCID 522689	—
Reactant	(Trifluoromethyl)trimethylsilane	HCID 552549	—
Reactant	3,5-Dibromo-2-iodopyridine	HCID 26967552	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	3,5-Dibromo-2-(trifluoromethyl)pyridine	HCID 11044942	46.1%

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a solution of 2-iodo-3,5-dibromopyridine (4.21 g, 11.60 mmol) in NMP (25 mL) were added copper(I)iodide (4.42 g, 23.21 mmol), potassium fluoride (1.35 g, 23.21 mmol), and (trifluoromethyl)trimethylsilane (5.61 mL, 35.90 mmol). The resulting mixture was allowed to stir overnight at 50° C. The mixture was poured into 12% aqueous ammonia, and then extracted with Et2O (2×120 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3,5-dibromo-2-(trifluoromethyl)pyridine (1.63 g, 46%) as a liquid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07998952B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-2f7cc3c2b32c4cf9a6a5cb63f60063f2
Source note	uspto-grants-2011_08