Hydrogen Peroxide → Methyl 3-bromo-4-carbamoylbenzoate

HRID 906165Notes

Reaction equation

HRID 906165 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[N:13])[C:5]([O:7][CH3:8])=[O:6].OO.C(=O)([O-])[O-:17].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([NH2:13])=[O:17])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 23379143Methyl 3-bromo-4-cyanobenzoate

Product 1

HCID 67403808Methyl 3-bromo-4-carbamoylbenzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 3-bromo-4-cyanobenzoate (prepared as described in Wang, G. T. et al. Bioorg. Med. Chem. Lett. 2005, 15(1), 153(1) (130 mg, 0.54 mmol) was dissolved in DMSO (1.5 mL) and was cooled in a cold water bath. 30% aqueous hydrogen peroxide (0.1 mL) and potassium carbonate (23.9.0 mg, 0.17 mmol) were added and the mixture was stirred at room temperature for 18.5 h. The reaction mixture was partitioned between ethyl acetate and 10% aqueous lithium chloride. The aqueous portion was extracted with ethyl acetate. The combined organic portions were dried over sodium sulfate, filtered and concentrated to afford methyl 3-bromo-4-(aminocarbonyl)benzoate (quantitative yield) as a yellow oil. GCMS for C9H8BrNO3: 257, 259 (M+).

Workup

  1. temperaturewas cooled in a cold water bath
  2. customThe reaction mixture was partitioned between ethyl acetate and 10% aqueous lithium chloride
  3. extractionThe aqueous portion was extracted with ethyl acetate
  4. dry with materialThe combined organic portions were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-442cc15669214ae0a06a6d6efed24278
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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