Sodium Carbonate → 4-(4-Bromophenyl)pyridine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-Bromo-4-iodobenzene	HCID 11522	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	(Pyridin-4-yl)boronic acid	HCID 2734379	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(4-Bromophenyl)pyridine	HCID 616283	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

Pyridin-4-ylboronic acid (500 mg, 4.07 mmol), 1-bromo-4-iodobenzene (1.27 g, 4.47 mmol) and 2M Na2CO3 (6.1 ml, 12.2 mmol) were dissolved in 20 ml DMF and the solution was degassed 3 times. PdCl2(dppf) (149 mg, 0.203 mmol) was added and the mixture was stirred overnight at 80° C. The solution was cooled, poured into 100 ml NaHCO3 (sat.) and extracted 3 times with 20 ml ethyl acetate. The combined organic layers were then washed with 4× water, then dried with Na2SO4. 4-(4-bromophenyl)pyridine was obtained and used without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07279478B2
Source dataset	uspto-grants-2007_10
ORD ID	ord-93b3318f9d7043a489f2ccf5a0dca060
Source note	uspto-grants-2007_10