N-bromobutanimide → 2,4-Dichlorophenyl 4'-bromomethyl-4-biphenylyl ketone

HRID 1645809Notes

Reaction equation

HRID 1645809 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(#N)N(C)C>[Br:24][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])=[O:15])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 197420752,4-Dichlorophenyl 4'-methyl-4-biphenylyl ketone

Product 1

HCID 197420972,4-Dichlorophenyl 4'-bromomethyl-4-biphenylyl ketoneYield 89.3%

Reagents, catalysts & solvents 2

HCID 15112DimethylcyanamideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5.0 g of 2,4-dichlorophenyl 4'-methyl-4-biphenylyl ketone, 2.7 g of N-bromosuccinimide and 20 mg of azaisobutyronitrile in 70 mL of carbon tetrachloride was heated to boiling under reflux for 4 hours. The precipitated material was filtered off and the filtrate was evaporated. The residue was recrystallized from toluene/cyclohexane. There were obtained 5.5 g (89%) of 2,4-dichlorophenyl 4'-bromomethyl-4-biphenylyl ketone as a colorless solid with a m.p. of 92° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe precipitated material was filtered off
  4. customthe filtrate was evaporated
  5. customThe residue was recrystallized from toluene/cyclohexane

Sources & evidence

ORD record
ord-61797e4cfc4f45aea984a16133434fba
Source dataset
uspto-grants-1993_01
Patent number
US05177067

Reaction notes

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