Acetic Acid → 4,7-Dibromo-2-phenyl-2H-benzotriazole

HRID 2236070Notes

Reaction equation

HRID 2236070 reaction equation
[Br:1][C:2]1[C:3]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([NH2:9])[C:5]([Br:8])=[CH:6][CH:7]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(O)(=O)C>O>[Br:1][C:2]1[C:3]2[C:4](=[N:9][N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=2)[C:5]([Br:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12217721Iodo benzene diacetateHCID 586256393,6-Dibromo-2-phenylazo-phenylamine

Product 1

HCID 593012654,7-Dibromo-2-phenyl-2H-benzotriazoleYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 3,6-dibromo-2-phenylazo-phenylamine (120 mg, 0.34 mmol), iodobenzene diacetate (109 mg, 0.34 mmol), and acetic acid (5 mL) were added to a 1-neck 100-mL round bottom flask. The solution was stirred for 1 h at room temperature. The solvent was reduced with a rotary evaporator and the flask was stored at −19° C. for 16 h resulting in the formation of a solid cake. Water was added to the solid cake to dissolve the acid. A crystalline solid was collected by filtration and washed with water. GC/MS confirmed the solid as the desired product. Yield: 50%.

Workup

  1. customThe solvent was reduced with a rotary evaporator
  2. waitthe flask was stored at −19° C. for 16 h
  3. customresulting in the formation of a solid cake
  4. dissolutionto dissolve the acid
  5. filtrationA crystalline solid was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-86f877b2400b4dd5beecef5c38502cec
Source dataset
uspto-grants-2010_05
Patent number
US07714099B2

Reaction notes

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