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

HRID 561205Notes

Reaction equation

HRID 561205 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 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 extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e0d3e198373493dbb594d99fad059e6
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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