1-Bromo-2-Chloroethane → diphenylmethanone O-(2-chloroethyl)oxime

HRID 484323

Reaction equation

HRID 484323 reaction equation
[C:1](=[N:14][OH:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:19][CH2:18][CH2:17][O:15][N:14]=[C:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11324Benzophenone oximeHCID 11430Potassium Carbonate

Product 1

HCID 10539239diphenylmethanone O-(2-chloroethyl)oximeYield 73.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzophenone oxime (3.94 g, 20 mmol), 1-bromo-2-chloroethane (28.7 g. 200 mmol) and dried, powdered potassium carbonate (5.53 g, 80 mmol) in acetone (60 ml) were heated at reflux for 72 h. The reaction mixture was cooled and filtered and the filtrate was evaporated to an oily residue which was purified by "flash" chromatography (eluting with heptane/ethyl acetate 19/1) to provide diphenylmethanone O-(2-chloroethyl)oxime (3.82 g, 73%) as an oil, tlc rf 0.36 (SiO2, heptane/ethyl acetate 9/1).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 72 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate was evaporated to an oily residue which
  6. customwas purified by "flash" chromatography (eluting with heptane/ethyl acetate 19/1)

Sources & evidence

ORD record
ord-76a41c95460d48beb8fa6acdf9d7653f
Source dataset
uspto-grants-1993_07
Patent number
US05231106

Linked notes

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