2-Methylnaphthalene → 2-Bromomethylnaphthalene

HRID 482643Notes

Reaction equation

HRID 482643 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Br:12]N1C(=O)CCC1=O.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 70552-MethylnaphthaleneHCID 11439SuccinimideHCID 67184N-bromobutanimide

Product 1

HCID 703202-BromomethylnaphthaleneYield 101.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 250 g (1.75 m) of 2-methylnaphthalene and 312.5 g (1.75 m) of N-bromosuccinimide in 1125 ml of carbon tetrachloride in a 3 liter round bottom flask fitted with a stirrer and reflux condenser with a drying tube was refluxed for twenty hours. The insoluble succinimide (171 g, 1.73 moles) was filtered and washed with 250 ml of carbon tetrachloride. Concentrated in vacuo gave 395 g of an oil to which was added 800 ml of petroleum ether. Solid crystallized immediately and was filtered and washed with 500 ml of petroleum ether. The first crop was air-dried to give 298 g, m.p. 48°-65° C. (Lit. m.p. 56° ). Concentration of the filtrate led to the isolation of another 33 g, m.p. 45°-50° C. of product to give a total of 331 g (86%) of good quality crude product.

Workup

  1. customfitted with a stirrer
  2. temperaturereflux condenser with a drying tube
  3. temperaturewas refluxed for twenty hours
  4. washwashed with 250 ml of carbon tetrachloride
  5. concentrationConcentrated in vacuo

Sources & evidence

ORD record
ord-e23e751cd6fb4c149fa798d6c2e3b447
Source dataset
uspto-grants-1986_03
Patent number
US04574125

Reaction notes

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