Hydrogen Peroxide → 2,5-Difluoro-4-[4-chloro-3-(trifluoromethyl)phenylmethoxy]-benzamide

HRID 508447Notes

Reaction equation

HRID 508447 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)[C:7]([F:23])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-:25].[K+].[K+].OO.O>CS(C)=O>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:20])([F:22])[F:21])[CH:13]=2)[C:7]([F:23])=[CH:6][C:3]=1[C:4]([NH2:5])=[O:25]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 866825572,5-Difluoro-4-[4-chloro-3-(trifluoromethyl)phenylmethoxy]-benzonitrile

Product 1

HCID 866825582,5-Difluoro-4-[4-chloro-3-(trifluoromethyl)phenylmethoxy]-benzamideYield 87.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 2,5-difluoro-4-[4-chloro-3-(trifluoromethyl)phenylmethoxy]-benzonitrile (Preparation 61, 0.2 g, 0.5 mmol) and potassium carbonate (0.39 g, 2.5 mmol) in DMSO (3 mL), was added hydrogen peroxide (30% solution in water, 0.6 mL, 5 mmol) at room temperature. The resulting mixture was stirred for 3 hours at room temperature. Water (30 mL) was then added and the precipitate formed was filtered. The filtrate was extracted twice with EtOAc and combined with the solid. The resulting organic solution was dried over magnesium sulphate, filtered and evaporated to afford the title compound as a white solid (160 mg, 76%).

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered
  3. extractionThe filtrate was extracted twice with EtOAc
  4. dry with materialThe resulting organic solution was dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-26e32dd0d1a54eea980f081ad77e1cf6
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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