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

HRID 484097

Reaction equation

HRID 484097 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) a nd 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-0c32900aead2417c8b28d283415f01e8
Source dataset
uspto-grants-1993_07
Patent number
US05229404

Linked notes

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