Phosphorus oxybromide → 4-Bromo-2-[3-(trifluoromethyl)phenyl]-1(2H)-phthalazinone

HRID 1765370Notes

Reaction equation

HRID 1765370 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][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:3]=1.P(Br)(Br)([Br:25])=O>O>[Br:25][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][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178515030HCID 178515030, compound

Product 1

HCID 211065474-Bromo-2-[3-(trifluoromethyl)phenyl]-1(2H)-phthalazinoneYield 67.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxy-2-(3-trifluoromethylphenyl)-2H-phthalazin-1-one (0.50 g, 1.6 mmol) and phosphorus oxybromide (1.9 g, 6.5 mmol) were stirred at 150° C. for 2 h. H2O (100 ml) was added after cooling to room temperature. The precipitated solid was collected by filtration and washed with H2O. Drying of the solid in vacuum gave the title compound (0.4 g, 66% yield). 1H-NMR: (400 MHz, D6-DMSO) 8.39 (1H, d), 7.95–8.12 (5H, m), 7.79–7.99 (2H, m); MS (ESI+)=370.98 (M+H)+.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with H2O
  3. customDrying of the solid in vacuum

Sources & evidence

ORD record
ord-cef38c92073f4f528585b627af2799eb
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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