Phosphorus oxychloride → 2-Chloro-4-(4-isopropyl-phenyl)-pyridine

HRID 628834Notes

Reaction equation

HRID 628834 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N+:13]([O-])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:14]1[CH:15]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)[CH:11]=[CH:12][N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 692333644-(4-isopropyl-phenyl)-pyridine-N-oxide

Product 1

HCID 837125462-Chloro-4-(4-isopropyl-phenyl)-pyridineYield 81%

Procedure

Part C. A mixture of 4-(4-isopropyl-phenyl)-pyridine-N-oxide (126 mg, 0.59 mmol) and phosphorus oxychloride (5 mL) is heated to reflux for 12 h. The mixture is cooled and evaporated, and the residue is dissolved in water, neutralized with satd. aq. Na2CO3 and extracted with ethyl acetate. The extract is washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue is separated by column chromatography to afford 2-chloro-4-(4-isopropyl-phenyl)-pyridine (110 mg, 81%).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 12 h
  3. temperatureThe mixture is cooled
  4. customevaporated
  5. dissolutionthe residue is dissolved in water
  6. extractionaq. Na2CO3 and extracted with ethyl acetate
  7. washThe extract is washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is separated by column chromatography

Sources & evidence

ORD record
ord-3f2045c82e4047d59ed442d9e6226058
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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