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

HRID 249284

Reaction equation

HRID 249284 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-2aadbcde41964545a79ea102d758d660
Source dataset
uspto-grants-1993_05
Patent number
US05214054

Linked notes

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