Water → Ethyl 3-bromo-4,5-dihydro-1,2-oxazole-5-carboxylate

HRID 1753976Notes

Reaction equation

HRID 1753976 reaction equation
[OH:1][N:2]=[C:3]([Br:5])Br.[C:6]([O:10][CH2:11][CH3:12])(=[O:9])[CH:7]=[CH2:8].O>CN(C=O)C>[Br:5][C:3]1[CH2:8][CH:7]([C:6]([O:10][CH2:11][CH3:12])=[O:9])[O:1][N:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8821Ethyl AcrylateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromide

Product 1

HCID 66696825Ethyl 3-bromo-4,5-dihydro-1,2-oxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a vigorously stirred mixture of hydroxycarbonimidic dibromide (15.5 g, 76.4 mmol) and ethyl acrylate (15.3 g, 153 mmol) in DMF (200 mL) was added a solution of 15 wt % aqueous KHCO3 (102 mL, 153 mmol). The mixture was stirred at room temperature overnight. Water was added and the mixture was extracted twice with methyl tert-butyl ether. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound.

Workup

  1. extractionthe mixture was extracted twice with methyl tert-butyl ether
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01886cecddd44e6da11f79cb84498f18
Source dataset
uspto-grants-2015_10
Patent number
US09168248B2

Reaction notes

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