Benzoyl Peroxide → 4-(Bromomethyl)benzophenone

HRID 435831Notes

Reaction equation

HRID 435831 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(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](=[O:7])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[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 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 19.6 g. (0.1 mole) 4-methyl benzophenone 17.8 g. (0.1 mole) N-bromosuccinimide, 0.4 g. (0.0016 mole) benzoyl peroxide and 200 ml. carbon tetrachloride is refluxed for 18 hours. The mixture is then cooled and filtered, and the resulting solid is suspended in water, filtered and washed with water. The wet solid is dissolved in methylene chloride, washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to give α-bromo-4-benzoyl toluene, m.p. 104° to 109° C.

Workup

  1. additionA mixture of 19.6 g
  2. temperatureThe mixture is then cooled
  3. filtrationfiltered
  4. filtrationfiltered
  5. washwashed with water
  6. dissolutionThe wet solid is dissolved in methylene chloride
  7. washwashed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-9fe46320a92b43858ab1f2aa68bf2bbc
Source dataset
uspto-grants-1977_02
Patent number
US04006248

Reaction notes

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