Dichloromethane → 4,5-dibromo-2-(4-hydroxyphenyl)-2H-pyridazin-3-one

HRID 15047Notes

Reaction equation

HRID 15047 reaction equation
ClCCl.B(Br)(Br)Br.[Br:8][C:9]1[C:10](=[O:24])[N:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[N:12]=[CH:13][C:14]=1[Br:15]>O>[Br:8][C:9]1[C:10](=[O:24])[N:11]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[N:12]=[CH:13][C:14]=1[Br:15]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 631734334,5-Dibromo-2-(4-methoxyphenyl)pyridazin-3(2H)-one

Product 1

HCID 684287654,5-dibromo-2-(4-hydroxyphenyl)-2H-pyridazin-3-oneYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1N dichloromethane solution (5.5 mL) of boron tribromide was added to a dichloromethane solution (30 mL) of 4,5-dibromo-2-(4-methoxyphenyl)-2H-pyridazin-3-one (1.1 g, 3.06 mmols), and stirred overnight at room temperature. Water (30 mL) was added and stirred for 30 minutes. The resulting precipitate was recovered by filtration, washed with water and chloroform and dried to provide the title compound (1.03 g, 97%).

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe resulting precipitate was recovered by filtration
  3. washwashed with water and chloroform
  4. customdried

Sources & evidence

ORD record
ord-3d9d0cf7ddde471781a2540f0cc9ffef
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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