Phosphorus oxybromide → 4-Bromo-2-(4-isopropylphenyl)-2H-phthalazin-1-one

HRID 1765365Notes

Reaction equation

HRID 1765365 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)[N:3]=1.P(Br)(Br)([Br:24])=O.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>O>[Br:24][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)[N:3]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 178439203HCID 178439203, compound

Product 1

HCID 211065534-Bromo-2-(4-isopropylphenyl)-2H-phthalazin-1-oneYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxy-2-(4-isopropylphenyl)-2H-phthalazin-1-one (0.10 g, 0.36 mmol), phosphorus oxybromide (0.41 g, 1.4 mmol) and 2,6-di-tert-butyl-4-methylphenol (0.02 g, 0.09 mmol) were stirred at 150° C. for 30 min. H2O (100 ml) was added after cooling to room temperature. Extraction with dichloromethane, drying of the combined organic phases over Na2SO4 and evaporation of the solvent yielded the desired compound (0.05 g, 41%) which was used without any further characterization.

Workup

  1. extractionExtraction with dichloromethane
  2. dry with materialdrying of the combined organic phases over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-397833bfd4b249429ac7f3d35be299c2
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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