Potassium Iodide → 1,2-diphenylethanone O-(2-bromoethyl)oxime

HRID 975249Notes

Reaction equation

HRID 975249 reaction equation
[C:1]1([C:7](=[N:15][OH:16])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.O>[Br:17][CH2:18][CH2:19][O:16][N:15]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 2353831,2-Diphenyl-1-ethanone oxime

Product 1

HCID 544627271,2-diphenylethanone O-(2-bromoethyl)oxime

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of the above oxime (5.0 g, 24 mmol), 1,2-dibromoethane (25 ml) and potassium carbonate (10.0 g, 72 mmol) in acetone (25 ml) was heated at reflux for 1 h, then stirred at ambient temperature for 72 h and finally heated at reflux for 4.5 h. Potassium iodide (0.5 g) was added and refluxing continued for an additional 16 h. Water (100 ml) was added and the resulting mixture extracted with dichloromethane (2×100 ml). The combined organic phases were washed with water (100 ml) and brine (10 ml) and dried (MgSO4). The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel (60 g, n-heptane/ethyl acetate 10/1) to give 3.6 g of 1,2-diphenylethanone O-(2-bromoethyl)oxime.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. temperaturefinally heated
  4. temperatureat reflux for 4.5 h
  5. temperaturerefluxing
  6. waitcontinued for an additional 16 h
  7. extractionthe resulting mixture extracted with dichloromethane (2×100 ml)
  8. washThe combined organic phases were washed with water (100 ml) and brine (10 ml)
  9. dry with materialdried (MgSO4)
  10. customThe solvent was evaporated in vacuo
  11. customthe residue was purified by column chromatography on silica gel (60 g, n-heptane/ethyl acetate 10/1)

Sources & evidence

ORD record
ord-6fa59199fd4b47ce95560c8b2553ec22
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Reaction notes

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