Phosphorus pentachloride → 2-Chloro-5-(trifluoromethyl)nicotinonitrile

HRID 981044

Reaction equation

HRID 981044 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)#[N:2].N1C=CC=CC1=O.P(Cl)(Cl)(Cl)(Cl)[Cl:21]>>[Cl:21][C:4]1[C:3]([C:1]#[N:2])=[CH:8][C:7]([C:9]([F:12])([F:10])[F:11])=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 67923873HCID 67923873, compound

Product 1

HCID 200715992-Chloro-5-(trifluoromethyl)nicotinonitrile

Procedure

A mixture of 3-cyano-5-trifluoromethylpyrdine-2-pyridone (250 mg), phosphorus pentachloride (550 mgs) and phosphonylchloride (0.62 ml) were heated at the reflux temperature for 8 hours. After cooling to ambient temperature (ca 28° C.) the reaction mixture was poured into ice/water and rigourously extracted with ethylacetate. The combined organic layers were washed with aqueous sodium bicarbonate solution followed by brine, and finally dried over anhydrous magnesium sulphate. Removal of the solvent by evaporation under reduced pressure gave 2-chloro-3-cyano-5trifluoromethyl-pyridine as an off-white solid which was used without further purification. The compound showed (CDC13) 8.89 (1H,d) 8.28 (1H,d).

Workup

  1. temperaturewere heated at the reflux temperature for 8 hours
  2. extractionrigourously extracted with ethylacetate
  3. washThe combined organic layers were washed with aqueous sodium bicarbonate solution
  4. dry with materialfinally dried over anhydrous magnesium sulphate
  5. customRemoval of the solvent
  6. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-4c8ee25da2514c308448319c0a528099
Source dataset
uspto-grants-1991_02
Patent number
US04990512

Linked notes

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