N-bromobutanimide → 2-(1-Naphthyl)benzyl bromide

HRID 1383803Notes

Reaction equation

HRID 1383803 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:18]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][Br:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 3016790(Methylphenyl)naphthalene

Product 1

HCID 110773332-(1-Naphthyl)benzyl bromideYield 91.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

114 g (0.52 mol) of 18 and 103 g (0.58 mol) of N-bromo-succinimide were dissolved in 2000 cm3 of tetrachloro-methane at room temperature, 3 g of azobisisobutyro-nitrile were added, and the mixture was refluxed for 4 hours. The succinimide which precipitated was filtered off, the solvent was removed in vacuo, and the residue was purified by filtration through 1000 g of silica gel (hexane/methylene chloride 9:1), giving 141 g (82%) of 19 as a colorless lachrymatory oil.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe succinimide which precipitated
  3. filtrationwas filtered off
  4. customthe solvent was removed in vacuo
  5. filtrationthe residue was purified by filtration through 1000 g of silica gel (hexane/methylene chloride 9:1)

Sources & evidence

ORD record
ord-dfb2583b2ab843199f0eaf934c6f13c6
Source dataset
uspto-grants-2001_07
Patent number
US06255506B1

Reaction notes

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