Benzoyl Peroxide → 4-(Bromomethyl)benzophenone

HRID 533496Notes

Reaction equation

HRID 533496 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(#N)C>[Br:16][CH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 86524-MethylbenzophenoneHCID 67184N-bromobutanimide

Product 1

HCID 1229514-(Bromomethyl)benzophenone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

4-Methyl benzophenone (product of Aldrich) (25.1 parts), N-bromo succinimide [product of Wako Pure Chemical industries, Ltd.] (22.8 parts), benzoyl peroxide [water content: 20%, product of Wako Pure Chemical Industries, Ltd.] (0.54 parts), and acetonitrile (80 parts) were mixed, heated to 80° C., and allowed to react for 2 hours under reflux. Subsequently, the resulting mixture was cooled, and the organic solvent was evaporated under reduced pressure. The residue was recrystallized in methanol (160 parts). As a result, 26 parts of an intermediate (C123-6-1) was obtained (as white crystals).

Workup

  1. customto react for 2 hours
  2. temperatureunder reflux
  3. temperatureSubsequently, the resulting mixture was cooled
  4. customthe organic solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized in methanol (160 parts)
  6. customAs a result, 26 parts of an intermediate (C123-6-1) was obtained (as white crystals)

Sources & evidence

ORD record
ord-a4649a9d08a34b50af0abca997f24276
Source dataset
uspto-grants-2014_10
Patent number
US08853290B2

Reaction notes

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