Phosphorus oxychloride → HCID 19791116, compound

HRID 1655218Notes

Reaction equation

HRID 1655218 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([CH3:9])=[N+:6]([O-])[CH:7]=1.P(Cl)(Cl)([Cl:13])=O>>[Br:1][C:2]1[C:3]([Cl:13])=[C:4]([CH3:10])[C:5]([CH3:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19791167HCID 19791167, compound

Product 1

HCID 19791116HCID 19791116, compound

Procedure

5-bromo-2,3-lutidine-N-oxide (30.31 g) was added in portions to phosphorus oxychloride (41.3 ml) at 30°-40°. The mixture was heated to 50°, when an exothermic reaction raised the temperature to reflux. After 30 minutes the solution was cooled and poured onto ice to give a white solid, which was filtered off and discarded. The filtrate was extracted with ether then treated with 40% aqueous sodium hydroxide to pH 7, and extracted again with ether. The latter extract was dried (MgSO4) and stripped to give 5-bromo-4-chloro-2,3-lutidine, 12.0 g as a low melting solid.

Workup

  1. temperatureThe mixture was heated to 50°
  2. customwhen an exothermic reaction
  3. temperatureraised the temperature
  4. temperatureto reflux
  5. temperatureAfter 30 minutes the solution was cooled
  6. additionpoured onto ice
  7. customto give a white solid, which
  8. filtrationwas filtered off
  9. extractionThe filtrate was extracted with ether
  10. additionthen treated with 40% aqueous sodium hydroxide to pH 7
  11. extractionextracted again with ether
  12. extractionThe latter extract
  13. dry with materialwas dried (MgSO4)

Sources & evidence

ORD record
ord-53692ee2451a469480a262dbd537e6d3
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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