Phosphorus oxychloride → 3-(3-Bromo-4-methoxyphenyl)-6-chloropyridazine

HRID 1763578Notes

Reaction equation

HRID 1763578 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=O)[NH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].P(Cl)(Cl)([Cl:19])=O>>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[N:14][C:13]([Cl:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 121965636-(3-Bromo-4-methoxyphenyl)-3(2H)-pyridazinone

Product 1

HCID 122575033-(3-Bromo-4-methoxyphenyl)-6-chloropyridazine

Procedure

A suspension of 100 g. of 6-(3-bromo-4-methoxyphenyl)-3(2H)-pyridazinone [J. Heterocyclic Chem. 11, 775 (1974) ]in 150 ml. of phosphorus oxychloride is refluxed until a clear solution is obtained (approximately 5 hours). The solution is cooled and excess phosphorus oxychloride is removed under vacuum to give a brown solid which is triturated with ice water. The solid is collected by filtration and is recrystallized to afford 3-(3-bromo-4-methoxyphenyl)-6-chloropyridazine.

Workup

  1. additionA suspension of 100 g
  2. customis obtained (approximately 5 hours)
  3. temperatureThe solution is cooled
  4. customexcess phosphorus oxychloride is removed under vacuum
  5. customto give a brown solid which
  6. customis triturated with ice water
  7. filtrationThe solid is collected by filtration
  8. customis recrystallized

Sources & evidence

ORD record
ord-262367b5719642fcbfb863d0973c56b2
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

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