4-Bromophenol → 3-(4-bromophenoxy)-6-(1H-imidazol-1-yl)pyridazine

HRID 359420Notes

Reaction equation

HRID 359420 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:6][CH:7]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[N:3]=[N:4][C:5]([N:8]3[CH:12]=[CH:11][N:10]=[CH:9]3)=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 10340Sodium CarbonateHCID 27709033-Chloro-6-(1H-imidazol-1-yl)pyridazine

Product 1

HCID 151247883-(4-bromophenoxy)-6-(1H-imidazol-1-yl)pyridazine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4.5 parts of 3-chloro-6-(1H-imidazol-1-yl)pyridazine, 3.2 parts of 4-bromophenol, 4.2 parts of sodium carbonate and 80 parts of 2-propanone was stirred and refluxed over weekend. The reaction mixture was evaporated and the residue was taken up in water and 2,2'-oxybispropane. The layers were separated. The organic phase was dried, filtered and evaporated. The residue was crystallized from 2-propanol, yielding 3.5 parts of 3-(4-bromophenoxy)-6-(1H-imidazol-1-yl)pyridazine; mp. 168.4° C. (compound 6).

Workup

  1. temperaturerefluxed over weekend
  2. customThe reaction mixture was evaporated
  3. customThe layers were separated
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-dbc477d55f6f479886f0d5a4ea5970ec
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Reaction notes

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