Phosphorus oxychloride → 2-Chloro-4-(trifluoromethyl)quinoline

HRID 2405776Notes

Reaction equation

HRID 2405776 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5](O)[CH:4]=1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:5]1[CH:4]=[C:3]([C:2]([F:15])([F:14])[F:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516126HCID 178516126, compound

Product 1

HCID 27829122-Chloro-4-(trifluoromethyl)quinolineYield 78%

Procedure

A round bottom was charged with 4-trifluoromethyl-quinolin-2-ol (1 g, 4.69 mmol) and POCl3 (10 ml, 107.28 mmol). The mixture was heated to reflux for 3 hours, and then concentrated to remove excess POCl3. The mixture was based with 5 N NaOH and extracted with DCM. The mixture was purified by flash chromatography to give intermediate 2-chloro-4-trifluoromethyl-quinoline (845 mg, 78%): LCMS found 232.22 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated
  4. customto remove excess POCl3
  5. extractionextracted with DCM
  6. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-fbd265303955421bbb8e3351c95565b6
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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