N-bromobutanimide → 2-[2-(Bromomethyl)phenyl]naphthalene

HRID 1383806Notes

Reaction equation

HRID 1383806 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].[Br:18]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][Br:18]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 210519422-(2-Naphthyl)toluene

Product 1

HCID 226765282-[2-(Bromomethyl)phenyl]naphthaleneYield 79%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

105 g (0.48 mol) of 25 and 90 g (0.5 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 112 g (79%) of 26 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-85b371976acf4a2aa4244542a68e936d
Source dataset
uspto-grants-2001_07
Patent number
US06255506B1

Reaction notes

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