Dimethylformamide → 3-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one

HRID 456192Notes

Reaction equation

HRID 456192 reaction equation
[O:1]1[CH2:5][C:4](=O)[N:3]=[C-:2]1.[H-].[Na+].[Br:9][C:10]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:11]=1[CH2:12]Br.CN(C=[O:26])C>CCOC(C)=O.O>[Br:9][C:10]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:11]=1[CH2:12][N:3]1[CH2:4][CH2:5][O:1][C:2]1=[O:26]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27562491-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzeneHCID 532495662H-1,3-oxazol-2-id-4-one

Product 1

HCID 668919133-(2-Bromo-5-trifluoromethyl-benzyl)-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 2-oxazolidone (0.110 g, 1.26 mmol) in DMF (4 mL) was added sodium hydride (60% in mineral oil; 0.056 g, 1.39 mmol), and the mixture was stirred at 0° C. for 10 minutes. 2-Bromo-5-(trifluoromethyl)benzyl bromide (0.420 g, 1.26 mmol) was added, and the reaction was stirred at 0° C. for 1 hour. The mixture was diluted with EtOAc and H2O, and the aqueous layer was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give the title compound.

Workup

  1. stirringthe reaction was stirred at 0° C. for 1 hour
  2. customthe aqueous layer was separated
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c90e3a82c8d24d33ae84f2ad3321c5b8
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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