Hydrogen Peroxide → 4-((3,4-Dichlorophenoxy)methyl)-2,5-difluorobenzamide

HRID 508433Notes

Reaction equation

HRID 508433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:5][CH2:6][C:7]1[C:14]([F:15])=[CH:13][C:10]([C:11]#[N:12])=[C:9]([F:16])[CH:8]=1.C(=O)([O-])[O-:22].[K+].[K+].OO>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:5][CH2:6][C:7]1[C:14]([F:15])=[CH:13][C:10]([C:11]([NH2:12])=[O:22])=[C:9]([F:16])[CH:8]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 666676954-((3,4-Dichlorophenoxy)methyl)-2,5-difluorobenzonitrile

Product 1

HCID 666672344-((3,4-Dichlorophenoxy)methyl)-2,5-difluorobenzamideYield 38%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 4-((3,4-dichlorophenoxy)methyl)-2,5-difluorobenzonitrile (Preparation 23, 153 mg, 0.481 mmol) in DMSO (5 mL) was added potassium carbonate (133 mg, 0.962 mmol), followed by dropwise addition of 30% aqueous hydrogen peroxide solution (0.29 mL, 2.90 mmol). After 3 hours, the reaction was quenched with saturated aqueous potassium bisulphate solution (10 mL), and extracted with DCM (3×10 mL). The combined organics were washed with brine (2×10 mL), dried over magnesium sulphate, and concentrated in vacuo to afford the title compound as a white solid (60 mg, 38%).

Workup

  1. customthe reaction was quenched with saturated aqueous potassium bisulphate solution (10 mL)
  2. extractionextracted with DCM (3×10 mL)
  3. washThe combined organics were washed with brine (2×10 mL)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d8a436f93d945e2a37cd0876fb748ef
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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