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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1958554Generated: October 29, 2026

Triethylamine → 2-Chloro-5-fluoropyridine-3-carbonitrile

https://huagongshe.com/reaction/1958554

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantTrifluoroacetic anhydrideHCID 9845—
Reactant2-Chloro-5-fluoropyridine-3-carboxamideHCID 12629796—
SolventDichloromethaneHCID 6344—
Product2-Chloro-5-fluoropyridine-3-carbonitrileHCID 2311085186%

Reaction Conditions

Temperature0 °C

Reaction Steps

A suspension of crude compound 3 (65 g, 372.4 mmol) and Et3N (114 mL, 819.2 mmol) in DCM (700 mL) was cooled to 0° C. and TFAA (57 mL, 409.6 mmol) was added dropwise. The resulting yellow solution was stirred for 90 minutes at 0° C., diluted with DCM, washed with sat. aq. NaHCO3 and brine, and dried (Na2SO4). The mixture was filtered and concentrated. Kugel Rohr distillation of the residue (˜70° C./1 mbar) gave 50 g (86%) of compound 4 as a beige solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08410133B2
Source datasetuspto-grants-2013_04
ORD IDord-62e7b588366944c9b4d77f15a438eede
Source noteuspto-grants-2013_04