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

HRID 1783680Notes

Reaction equation

HRID 1783680 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 RT. Extraction with DCM, 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 DCM
  2. dry with materialdrying of the combined organic phases over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-9390d35bf1aa41e2a0d7f442265d59bb
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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