Benzoyl Peroxide → HCID 19699931, compound

HRID 863203Notes

Reaction equation

HRID 863203 reaction equation
[C:1]([O:4][C:5]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])(=[O:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:18]=[C:17]([CH2:19][Br:20])[CH:16]=[CH:15][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19699940HCID 19699940, compound

Product 1

HCID 19699931HCID 19699931, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture comprising 1.3 g of the 2-acetoxy-4-methylbenzophenone prepared in the step (c), 910 mg of N-bromosuccinimide and 20 ml of carbon tetrachloride was heated under reflux together with a small amount of benzoyl peroxide for one hour. The reaction mixture was cooled and filtered through a silica gel bed, and the silica gel was washed with 20% ethyl acetate/hexane. The filtrate and washings were concentrated together. The residue was subjected to silica gel column chromatography (7 to 10% ethyl acetate/hexane) to give 1.08 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through a silica gel bed
  4. washthe silica gel was washed with 20% ethyl acetate/hexane
  5. concentrationThe filtrate and washings were concentrated together

Sources & evidence

ORD record
ord-36d205c74689467d82a13ea4312aceac
Source dataset
uspto-grants-1998_02
Patent number
US05719303

Reaction notes

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