1-Methylnaphthalene → 1-(Bromomethyl)naphthalene

HRID 1174450Notes

Reaction equation

HRID 1174450 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70021-MethylnaphthaleneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide

Product 1

HCID 1378441-(Bromomethyl)naphthaleneYield 94%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 52.35 g (368.1 mmol) of 1-methylnaphthalene, 68.79 g (368.5 mmol) of N-bromosuccinimide (NBS), 0.45 g (1.86 mmol) of benzoyl peroxide (BPO) and 250 ml of carbon tetrachloride was stirred for 6 hours while heating and refluxing. The deposit was removed by filtration, and the filtrate was concentrated to obtain 84.64 g (purity: 90.4%, yield: 94%) of an oily crude product of 1-(bromomethyl)naphthalene.

Workup

  1. temperaturewhile heating
  2. temperaturerefluxing
  3. customThe deposit was removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ad74d5cace7347d685d0435d7d99b4fa
Source dataset
uspto-grants-2010_11
Patent number
US07838130B2

Reaction notes

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