Thionyl Chloride → 2,6-Dichloro-4-(trifluoromethyl)nicotinoyl chloride

HRID 2214984Notes

Reaction equation

HRID 2214984 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:18])=O>>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:3]=1[C:4]([Cl:18])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 219481962,6-Dichloro-4-(trifluoromethyl)nicotinic acid

Product 1

HCID 219482122,6-Dichloro-4-(trifluoromethyl)nicotinoyl chloride

Procedure

A solution of 2,6-dichloro-4-(trifluoromethyl)nicotinic acid (3.22 g, 13.2 mmol) in thionyl chloride (9 mL) was heated at reflux for 3 h. After cooling, the solution was concentrated in vacuo to give 2,6-dichloro-4-(trifluoromethyl)nicotinoyl chloride as a yellow 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-55dcf52b67784195b560253524bf01a3
Source dataset
uspto-grants-2006_09
Patent number
US07109196B2

Reaction notes

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