1,2-Dibromoethane → 2-methoxyacetophenone O-(2-bromoethyl)oxime

HRID 975242Notes

Reaction equation

HRID 975242 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[N:11][OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Br:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:13][CH2:14][CH2:15][O:12][N:11]=[C:4]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 740317252-Methoxyacetophenone oxime

Product 1

HCID 541510622-methoxyacetophenone O-(2-bromoethyl)oxime

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the above oxime (5.5 g, 33 mmol), 1,2-dibromoethane (50 ml), potassium carbonate (12.4 g, 90 mmol) and acetone (100 ml) was heated at reflux for 24 h. The mixture was filtered and the solvent was evaporated from the filtrate in vacuo. The residue was purified by column chromatography on silica gel (80 g, n-heptane/ethyl acetate 20/1) to give 6.6 g of 2-methoxyacetophenone O-(2-bromoethyl)oxime.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. filtrationThe mixture was filtered
  4. customthe solvent was evaporated from the filtrate in vacuo
  5. customThe residue was purified by column chromatography on silica gel (80 g, n-heptane/ethyl acetate 20/1)

Sources & evidence

ORD record
ord-1f4327bdd08844159eeee48e5172882e
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Reaction notes

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