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

HRID 2183764Notes

Reaction equation

HRID 2183764 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-5bcce8307bed47619cadab82dcd30e01
Source dataset
uspto-grants-2005_05
Patent number
US06900205B2

Reaction notes

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