Water → 5-bromo-3-methyl-3H-benzooxazol-2-one

HRID 1672838Notes

Reaction equation

HRID 1672838 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[C:12](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH3:12])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 268532-Benzoxazolinone, 5-bromo-

Product 1

HCID 3374695-bromo-3-methyl-3H-benzooxazol-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercially available 5-bromobenzo[d]oxazol-2(3H)-one (1.00 g, 4.67 mmol) was dissolved in DMF (23 mL), and the mixture was stirred at room temperature for 30 minutes after adding potassium carbonate (3.87 g, 28.0 mmol) and methyl iodide (0.87 mL, 14.0 mmol). Water was added to the mixture, and the mixture was stirred. The precipitated solid was filtered off and dried to give 5-bromo-3-methylbenzo[d]oxazol-2(3H)-one (839 mg, 79%).

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe precipitated solid was filtered off
  3. customdried

Sources & evidence

ORD record
ord-7290c68dea9e4314be671a7c1b0ad348
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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