Hydrogen Peroxide → 4-[4-Chloro-3-(trifluoromethyl)phenoxy]benzamide

HRID 2359314Notes

Reaction equation

HRID 2359314 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].C([O-])([O-])=[O:22].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH2:12])=[O:22])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:17]([F:18])([F:19])[F:20]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 580463154-(4-Chloro-3-(trifluoromethyl)phenoxy)benzonitrile

Product 1

HCID 580463404-[4-Chloro-3-(trifluoromethyl)phenoxy]benzamideYield 100.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-[4-chloro-3-(trifluoromethyl)phenoxy]benzonitrile (Preparation 47, 48 g, 161 mmol) in DMSO (500 ml) was added K2CO3 (45 g, 323 mmol) followed by dropwise addition of a 30 wt % aqueous hydrogen peroxide solution (27 ml, 806 mmol) at 15° C. The reaction mixture was stirred for 1 hour at room temperature and the mixture was poured into water (500 ml) to afford a preciptate. The precipitated solid was collected by filtration, azeotroped with toluene, and dried over in vacuo to give 51 g of titled compound.

Workup

  1. customto afford a preciptate
  2. filtrationThe precipitated solid was collected by filtration
  3. customazeotroped with toluene
  4. customdried over in vacuo

Sources & evidence

ORD record
ord-4e18c6a120ac414fb40edd4130ec4b8d
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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