Dimethylformamide → 5-Bromo-3-(4-fluorophenoxy)picolinonitrile

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	4-Fluorophenol	HCID 9732	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	5-Bromo-3-nitropyridine-2-carbonitrile	HCID 2769698	—
Solvent	Water	HCID 962	—
Product	5-Bromo-3-(4-fluorophenoxy)picolinonitrile	HCID 66995028	113.2%

Reaction Conditions

Temperature	0 °C

Reaction Steps

A flask was charged with 4-fluorophenol (44 g, 365 mmol) and DMF (500 mL). The reaction was cooled to 0° C. Sodium hydride (16.6 g, 414 mmol) was added and stirred for 10 minutes. 5-Bromo3-nitropicolinonitrile (90 g, 395 mmol) was added and the mixture stirred at ambient temperature for 30 minutes. The reaction was poured into a flask containing water (5000 mL) and stirred for 10 minutes. The pH was adjusted to 10 to give 5-Bromo-3-(4-fluorophenoxy)picolinonitrile (121 g, 413 mmol, 105% yield) as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08853409B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-e22b91ff687447d9a360ee86d3de5b57
Source note	uspto-grants-2014_10