Phosphorus oxychloride → 3-(4-Bromophenyl)-6-chloropyridazine

HRID 372693Notes

Reaction equation

HRID 372693 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=O)[NH:12][N:13]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:17])=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([Cl:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 6890736-(4-Bromophenyl)-2,3-dihydropyridazin-3-one

Product 1

HCID 64052553-(4-Bromophenyl)-6-chloropyridazine

Procedure

A mixture of 20.0 g. of 6-(p-bromophenyl)-3(2H)-pyridazinone (prepared as described in Example 1) in 100 ml. of phosphorus oxychloride is heated at reflux temperature for 41/2 hours. The excess phosphorus oxychloride is removed under reduced pressure and the residue is stirred with water-cracked ice to decompose the remaining phosphorus oxychloride. The product is recovered by filtration and recrystallized from dilute dimethylformamide yielding tan crystals, m.p. 201°-203° C.

Workup

  1. additionA mixture of 20.0 g
  2. temperatureat reflux temperature for 41/2 hours
  3. customThe excess phosphorus oxychloride is removed under reduced pressure
  4. filtrationThe product is recovered by filtration
  5. customrecrystallized from dilute dimethylformamide yielding tan crystals, m.p. 201°-203° C.

Sources & evidence

ORD record
ord-b086c842a9df4bda8a2409b0ce4d4654
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Reaction notes

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