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

HRID 1701348Notes

Reaction equation

HRID 1701348 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=[O:6].[Br:17]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 2

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

Product 1

HCID 136496533-(4-Chlorobenzoyl)benzyl bromideYield 62.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A mixture of 23.05 g of 3-methyl-4'-chlorobenzophenone, 70 cc of carbon tetrachloride, 16.02 g of N-bromosuccinimide and 90 mg benzoyl peroxide was refluxed for 4 hours and then was added to 100 cc of carbon tetrachloride. The mixture was filtered hot and the filter was washed with 100 cc of boiling carbon tetrachloride. 200 cc of the solvent were distilled off under reduced pressure and the mixture was cooled and iced for 1 hour. The mixture was vacuum filtered and the recovered crystals were empasted with iced carbon tetrachloride and dried under reduced pressure. The residue was crystallized from ethanol to obtain 17.5 g of 3-bromomethyl-4'-chlorobenzophenone melting at 138°-139° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationThe mixture was filtered hot
  3. washthe filter was washed with 100 cc of boiling carbon tetrachloride
  4. distillation200 cc of the solvent were distilled off under reduced pressure
  5. temperaturethe mixture was cooled
  6. filtrationfiltered
  7. customdried under reduced pressure
  8. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-c945a5de21bd4c249b9832dd9cf24537
Source dataset
uspto-grants-1980_03
Patent number
US04192890

Reaction notes

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