2,3-Dichloro-5-(trifluoromethyl)pyridine → 3-Chloro-2-fluoro-5-(trifluoromethyl)pyridine

HRID 897164Notes

Reaction equation

HRID 897164 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[F-:13].[K+]>CS(C)=O>[Cl:8][C:7]1[C:2]([F:13])=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

4

Reactant 2

HCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 522689Potassium Fluoride

Product 1

HCID 12680753-Chloro-2-fluoro-5-(trifluoromethyl)pyridineYield 92.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

2,3-Dichloro-5-trifluoromethylpyridine (800 g) was added to a stirred mixture of anhydrous potassium fluoride (320 g) and anhydrous dimethylsulphoxide at 110° C. then heated at 120° C. for 2 hours and fractionally distilled under reduced pressure to give 3-chloro-2-fluoro-5-trifluoromethylpyridine (685 g) in a yield of 92% (98% purity).

Workup

  1. distillationfractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-8d35ee869f354007a53ea8780377c22c
Source dataset
uspto-grants-2005_07
Patent number
US06921828B2

Reaction notes

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