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

HRID 2214988Notes

Reaction equation

HRID 2214988 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-943b2dc5ee5443f9bb4075afc30cc7dc
Source dataset
uspto-grants-2006_09
Patent number
US07109196B2

Reaction notes

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