2-Bromo-1-(3,4-dichlorophenyl)ethanone → HCID 58127683, compound

HRID 1257445Notes

Reaction equation

HRID 1257445 reaction equation
[NH2:1][C:2](=[S:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)=O>C(O)C>[Cl:26][C:21]1[CH:20]=[C:19]([C:17]2[N:1]=[C:2]([CH2:3][C:4]3[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=3)[S:14][CH:16]=2)[CH:24]=[CH:23][C:22]=1[Cl:25]

Participants

4

Reactant 2

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 58127823HCID 58127823, compound

Product 1

HCID 58127683HCID 58127683, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (209 mg, 1.0 mmol) obtained in Example 178a in ethanol (4 ml) was added 2-bromo-1-(3,4-dichlorophenyl)ethanone (268 mg, 1.00 mmol), and the mixture was heated under reflux for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with diluted aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (352 mg, 93%) as a yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with diluted aqueous sodium hydrogen carbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f805607cf6bd4ad0823634be6bd87b50
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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