Sodium Carbonate → 2-Chloro-5-(trifluoromethyl)pyridine

HRID 1413204Notes

Reaction equation

HRID 1413204 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:14])([F:13])[F:15])=[CH:8][N:7]=1.[Cl:3][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 178516044HCID 178516044, compound

Product 2

HCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 178516044HCID 178516044, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

30 g of thionyl chloride was added to 12 g of 2-hydroxy-5-trifluoromethylpyridine dissolved in 20 g of dimethylformamide. The 2-hydroxy-5-trifluoromethylpyridine was prepared as disclosed in Examples 4 and 5 of applicant's copending application earlier referred to and incorporated herein by reference. The solution was then heated to 60° C. for 24 hours, cooled to 20° C. and diluted with 200 cc of water and the pH adjusted to 5.5 with sodium carbonate. The acid solution was extracted three times with 100 cc of chloroform each time and the extracts washed three times with 20 cc of water each time. The chloroform solution was evaporated at reduced pressure to give 2-chloro-5-trifluoromethylpyridine.

Workup

  1. temperaturecooled to 20° C.
  2. extractionThe acid solution was extracted three times with 100 cc of chloroform each time
  3. washthe extracts washed three times with 20 cc of water each time
  4. customThe chloroform solution was evaporated at reduced pressure

Sources & evidence

ORD record
ord-646d01ba02c74014aa5e40930bcbad8b
Source dataset
uspto-grants-1981_02
Patent number
US04249009

Reaction notes

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