Phosphorus oxychloride → HCID 46311229, compound

HRID 509278Notes

Reaction equation

HRID 509278 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([O:11][CH3:12])=[O:10])=[N+:6]([O-])[CH:7]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:7]1[N:6]=[C:5]([C:9]([O:11][CH3:12])=[O:10])[CH:4]=[CH:3][C:2]=1[F:1]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 674680105-Fluoro-2-(methoxycarbonyl)pyridine 1-oxide

Product 1

HCID 46311229HCID 46311229, compoundYield 79%

Procedure

5-fluoro-2-(methoxycarbonyl)pyridine 1-oxide (100 mg, 0.584 mmol) was dissolved in POCl3 (2 ml), and then heated at reflux under nitrogen stream for 4 hours. The resulting reaction liquid was slowly added to ice (15 g), and then extracted with MC (30 ml×2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (20% EtOAc/Hexanes), to obtain 88 mg of white solid (79%).

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen stream for 4 hours
  3. customThe resulting reaction liquid
  4. extractionextracted with MC (30 ml×2)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfollowed by filtration and concentration
  7. customthe residue thus obtained

Sources & evidence

ORD record
ord-f0d0bfefd3a546539b94ba023fb586e8
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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