Dibromomethane → HCID 66817210, compound

HRID 1754985Notes

Reaction equation

HRID 1754985 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[CH2:12][OH:13])=[CH:6][C:5]=1[CH3:15].Br[CH2:17]Br>CN(C=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:11](=[O:14])[CH2:12][O:13][CH2:17]2)=[CH:6][C:5]=1[CH3:15]

Participants

5

Reactant 3

HCID 3024DibromomethaneHCID 24758Sodium hydrideHCID 16769056HCID 16769056, compound

Product 1

HCID 66817210HCID 66817210, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (81 mg, 1.80 mmol) was added to a solution of N-(4-bromo-3-methyl-phenyl)-2-hydroxy-acetamide (200 mg, 0.819 mmol) in DMF (4.0 ml), and the mixture was stirred at room temperature for 50 minutes. Further, dibromomethane (0.114 ml, 1.64 mmol) was added to the reaction solution, and the mixture was heated with stirring at 110° C. for two hours. Cooling to room temperature and subsequent purification by silica gel column chromatography (hexane-ethyl acetate) gave 3-(4-bromo-3-methyl-phenyl)-oxazolidin-4-one (45 mg, 21%).

Workup

  1. temperaturethe mixture was heated
  2. stirringwith stirring at 110° C. for two hours
  3. temperatureCooling to room temperature
  4. customsubsequent purification by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d0ed4efc1cf94f5e8187bab386d56641
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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