Hydrogen Peroxide → 3-Bromo-4-(5-formyl-pyridin-2-yloxy)-benzamide

HRID 130902Notes

Reaction equation

HRID 130902 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][N:12]=1)[C:5]#[N:6].C(=O)([O-])[O-:20].[K+].[K+].OO.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][N:12]=1)[C:5]([NH2:6])=[O:20]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 597299663-Bromo-4-(5-formyl-pyridin-2-yloxy)-benzonitrile

Product 1

HCID 597302773-Bromo-4-(5-formyl-pyridin-2-yloxy)-benzamideYield 100.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

Combine 3-bromo-4-(5-formyl-pyridin-2-yloxy)-benzonitrile (1.60 g, 5.28 mmol) and potassium carbonate (365 mg, 2.64 mmol) in DMSO (40 mL). Cool the reaction mixture at 0° C. Add hydrogen peroxide (1.59 mL, 5.28 mmol) dropwise and let the reaction stir at room temperature for 2 h. Pour into water and triturate to a white solid with stirring. Filter the white solid and dry to give (852 mg, 82%) of the title compound.

Workup

  1. customtriturate to a white solid
  2. stirringwith stirring
  3. filtrationFilter the white solid
  4. customdry

Sources & evidence

ORD record
ord-fae886514bc7458ca7ce333705aab840
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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