Phosphorus oxychloride → 2,6-Dichloro-5-fluoronicotinic acid

HRID 1590907Notes

Reaction equation

[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].P(Cl)(Cl)(Cl)=[O:14].[Li]>>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:14])=[O:5]

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 27336662,6-Dichloro-5-fluoro-3-pyridinecarbonyl chloride2×

HCID 3028194Lithium

Product 1

HCID 27336592,6-Dichloro-5-fluoronicotinic acid

Procedure

An improved process for the preparation of 2,6-dichloro-5-fluoronicotinoyl chloride is described where a 2,6-dihydroxy-5-fluoronicotinic acid ester is converted in one step using phosphorus oxychloride and a lithium reagent to 2,6-dichloro-5-fluoronicotinoyl chloride and subsequent basic hydrolysis affords 2,6-dichloro-5-fluoronicotinic acid.

Sources & evidence

ORD record: ord-0abbec808d7748bcac7d4a57eb1dbe36
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05204478

Reaction notes

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