Benzoyl Peroxide → HCID 23139035, compound

HRID 1171661Notes

Reaction equation

HRID 1171661 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([CH:12]1[CH2:14][CH2:13]1)=[O:11].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:15][CH:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[C:10]([CH:12]1[CH2:14][CH2:13]1)=[O:11]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 23138773853804-82-7

Product 1

HCID 23139035HCID 23139035, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-(2,4-difluorophenyl)-1-cyclopropylethanone (329 mg) in carbon tetrachloride (10 ml) was added N-bromosuccinimide (360 mg) and 75% benzoyl peroxide with stirring at room temperature, and the resulting mixture was refluxed for 3.5 hours. After the reaction mixture was filtrated, 1N aqueous sodium hydroxide solution was added to the filtrate. The resulting mixture was extracted with ethyl acetate, and the extract was washed with saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed in vacuo to afford the title compound (390 mg, yield: 84%) as a yellow oil.

Workup

  1. temperaturethe resulting mixture was refluxed for 3.5 hours
  2. filtrationAfter the reaction mixture was filtrated
  3. addition1N aqueous sodium hydroxide solution was added to the filtrate
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe extract was washed with saturated sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-194ac7653146420b868ad286e5a3f138
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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