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

HRID 1063521Notes

Reaction equation

HRID 1063521 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-8537e72a5a5c40ea83778bbd8c7eb354
Source dataset
uspto-grants-2005_11
Patent number
US06964971B2

Reaction notes

Loading…