N-bromobutanimide → HCID 19742105, compound

HRID 2255278Notes

Reaction equation

HRID 2255278 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(#N)N(C)C>[C:2]1([C:1]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][Br:22])=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)=[O:8])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11208026(4'-Methyl[1,1'-biphenyl]-4-yl)(phenyl)methanone

Product 1

HCID 19742105HCID 19742105, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 15112DimethylcyanamideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 26.1 g of 4-benzoyl-4'methylbiphenyl, 18.6 g of N-bromosuccinimide and 0.18 g of azaisobutyronitrile in 600 mL of carbon tetrachloride was heated to boiling for 4 hours. The brown solution obtained was filtered and evaporated. The residue was recrystallized from cyclohexane. There are obtained 29.9 g (89%) of 4'-(bromomethyl)-4-biphenylyl phenyl ketone as colorless crystals with a m.p. of 110°-112° C.

Workup

  1. temperaturewas heated
  2. customThe brown solution obtained
  3. filtrationwas filtered
  4. customevaporated
  5. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-46bbaa8a22574d16a51bfd59e182828e
Source dataset
uspto-grants-1993_08
Patent number
US05239084

Reaction notes

Loading…