Phosphorus oxychloride → 4,7-Dichloro-2-(trifluoromethyl)quinoline

HRID 1270775Notes

Reaction equation

HRID 1270775 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[N:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:19])=O.C([O-])(O)=O.[Na+]>>[Cl:19][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178516134HCID 178516134, compound

Product 1

HCID 184515164,7-Dichloro-2-(trifluoromethyl)quinoline

Procedure

A mixture of 7-chloro-2-trifluoromethyl-4-quinolinol (4 g, 16.2 mmol) in phosphorus oxychloride (7.55 mL, 81 mmol) is heated at reflux temperature for 3 hours. After cooling to room temperature, ice (200 g) is added, the mixture is neutralized with NaHCO3 and extracted with EtOAc. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator. The resulting tan residue is purified by flash chromatography on silica gel (1% ether in hexanes) to give 4,7-dichloro-2-trifluoromethylquinoline as a solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hours
  3. extractionextracted with EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated by rotary evaporator
  7. customThe resulting tan residue is purified by flash chromatography on silica gel (1% ether in hexanes)

Sources & evidence

ORD record
ord-0f3ca36928b5486b8a87ff3e61f1930d
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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