N-bromobutanimide → 3-(4-Chlorobenzoyl)benzyl bromide

HRID 280636Notes

Reaction equation

HRID 280636 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[CH2:14][Br:17])=[O:7])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27576664-Chloro-3'-methylbenzophenone

Product 1

HCID 136496533-(4-Chlorobenzoyl)benzyl bromideYield 57.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-(4-chlorobenzoyl)toluene (5.48 g, 23.7 mmol) and dibenzoylperoxide (100 mg, 0.413 mmol) in carbon tetrachloride (45 ml) was treated with N-bromosuccinimide (4.65 g, 26.7 mmol) and refluxed 2.5 hours. The mixture was filtered while hot and slowly cooled to ambient temperature. The precipitate was collected by filtration, washed twice with carbon tetrachloride, and dried under vacuum to provide 4.2 g (57%) of 3-(4-chlorobenzoyl)benzyl bromide, m.p. 123°-125° C.

Workup

  1. temperaturerefluxed 2.5 hours
  2. filtrationThe mixture was filtered while hot and
  3. filtrationThe precipitate was collected by filtration
  4. washwashed twice with carbon tetrachloride
  5. customdried under vacuum

Sources & evidence

ORD record
ord-def8e9af73b044d3a6471a3d3f9b9c5a
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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