Thionyl Chloride → 2-(2,5-Dichloro-phenoxy)-5-fluoro-nicotinoyl chloride

HRID 1877407Notes

Reaction equation

HRID 1877407 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[O:4][C:5]1[N:13]=[CH:12][C:11]([F:14])=[CH:10][C:6]=1[C:7](O)=[O:8].S(Cl)([Cl:22])=O>ClCCl>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[O:4][C:5]1[N:13]=[CH:12][C:11]([F:14])=[CH:10][C:6]=1[C:7]([Cl:22])=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 673674432-(2,5-Dichloro-phenoxy)-5-fluoro-nicotinic acid

Product 1

HCID 866412572-(2,5-Dichloro-phenoxy)-5-fluoro-nicotinoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,5-dichloro-phenoxy)-5-fluoro-nicotinic acid (2.14 g, 7.08 mmol, 1.0 equiv; Example 80, Step 1) in dichloromethane (15 mL) was added thionyl chloride (16.4 g, 10 mL, 138 mmol, 19.5 equiv; [CAS RN 7719-09-7]) and the reaction mixture heated to reflux for 2 h. The reaction mixture was concentrated under reduced pressure and remaining thionyl chloride removed by azotropic distillation with toluene. The crude material was used in the consecutive reaction step without further purification.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 2 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customremoved by azotropic distillation with toluene
  5. customThe crude material was used in the consecutive reaction step without further purification

Sources & evidence

ORD record
ord-667192e8f1cc4b27be8f2b9492723848
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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