Thionyl Chloride → 2,6-Dichloro-5-fluoro-3-pyridinecarbonyl chloride

HRID 2183768Notes

Reaction equation

HRID 2183768 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O>>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27336592,6-Dichloro-5-fluoronicotinic acid

Product 1

HCID 27336662,6-Dichloro-5-fluoro-3-pyridinecarbonyl chloride

Procedure

A solution of commercially available (Aldrich) 2,6-dichloro-5-fluoronicotinic acid (5.00 g, 23.8 mmol) in thionyl chloride (15 mL) was heated at reflux for 3 h. After cooling, the solution was concentrated in vacuo to give 2,6-dichloro-5-fluoronicotinoyl chloride as a brown oil which was carried on to the next step without further purification. This transformation can also be accomplished using oxalyl chloride with catalytic DMF in place of thionyl chloride.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-3dad9bd209934f0b9ab0e31b5bbdaa6e
Source dataset
uspto-grants-2005_05
Patent number
US06900205B2

Reaction notes

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