Phosphorus oxychloride → 3-(p-Bromophenyl)-6-chloro-4-methylpyridazine

HRID 372707Notes

Reaction equation

HRID 372707 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH3:15])=[CH:10][C:11](=O)[NH:12][N:13]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:18])=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([Cl:18])=[CH:10][C:9]=2[CH3:15])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 233336686-(p-bromophenyl)-5-methyl-3(2H)-pyridazinone

Product 1

HCID 203982893-(p-Bromophenyl)-6-chloro-4-methylpyridazine

Procedure

A 2.0 g. portion of 6-(p-bromophenyl)-5-methyl-3(2H)-pyridazinone and 20 ml. of phosphorus oxychloride are heated on a steam bath for 3 hours. The reaction mixture is poured slowly into crushed ice. The excess phosphorus oxychloride is decomposed. The solid which forms is recovered by filtration, washed with water, dried and recrystallized twice from chloroform, yielding 6-(p-bromophenyl)-5-methyl-3-chloropyridazine, m.p. 197°-200° C.

Workup

  1. additionThe reaction mixture is poured slowly
  2. custominto crushed ice
  3. filtrationThe solid which forms is recovered by filtration
  4. washwashed with water
  5. customdried
  6. customrecrystallized twice from chloroform

Sources & evidence

ORD record
ord-7e7c0c4026c44048b47fb1c593e43e72
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Reaction notes

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