Benzoyl Peroxide → 1-Bromo-2-(bromomethyl)naphthalene

HRID 1855971Notes

Reaction equation

HRID 1855971 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][Br:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 757541-Bromo-2-methylnaphthalene

Product 1

HCID 378281-Bromo-2-(bromomethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 100 parts of 1-bromo-2-methylnaphthalene, 80.5 parts of N-bromosuccinimide and 0.5 part of benzoyl peroxide in 1500 parts by volume of carbon tetrachloride is heated at reflux temperature for several hours. The solution is then cooled, washed twice with water and the organic layer separated. The organic layer is dried over calcium sulfate, filtered and concentrated to give 1-bromo-2-(bromomethyl)naphthalene, as an oil which solidifies on standing.

Workup

  1. temperatureat reflux temperature for several hours
  2. temperatureThe solution is then cooled
  3. washwashed twice with water
  4. customthe organic layer separated
  5. dry with materialThe organic layer is dried over calcium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dab7b4f380bf43f9823e975ff1d44baa
Source dataset
uspto-grants-1980_08
Patent number
US04217306

Reaction notes

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