Epibromohydrin → HCID 19020732, compound

HRID 1109523Notes

Reaction equation

HRID 1109523 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][N:14]=[C:13]([OH:16])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1.[CH2:17]([CH:19]1[O:21][CH2:20]1)Br>CN(C)C=O>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][N:14]=[C:13]([O:16][CH2:17][CH:19]3[O:21][CH2:20]3)[CH:12]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 10942334Sodium MethoxideHCID 178515585HCID 178515585, compound

Product 1

HCID 19020732HCID 19020732, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

29.6 g (0.153 moles) of sodium methoxide (as a 28% w/v methanolic solution) were added to a solution of 30.0 g (0.153 moles) of 5-(m-chlorophenyl)-3-hydroxyisoxazole in 300 ml of dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, 41.9 g (0.306 moles) of epibromohydrin were added dropwise, and the mixture was stirred for a further 3 days. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was diluted with ethyl acetate. The resulting mixture was washed with 800 ml of a 10% w/v aqueous solution of sodium chloride. The organic layer was then dried over anhydrous magnesium sulfate, the desiccant was removed by filtration, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, eluted with a 2:1 by volume mixture of benzene and ethyl acetate, to give a solid residue, which was recrystallized from diisopropyl ether, to give 23.6 g (yield 73.5%) of the title compound as colorless needles, melting at 86°-87° C.

Workup

  1. stirringthe mixture was stirred for a further 3 days
  2. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe resulting mixture was washed with 800 ml of a 10% w/v aqueous solution of sodium chloride
  5. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  6. customthe desiccant was removed by filtration
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography through silica gel
  9. washeluted with a 2:1 by volume mixture of benzene and ethyl acetate
  10. customto give a solid residue, which
  11. customwas recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8bc1e1f13aee4f55a73499144a0c501c
Source dataset
uspto-grants-1994_06
Patent number
US05321037

Reaction notes

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