2-Methylanisole → 4-Bromo-1-methoxy-2-methylbenzene

HRID 249279

Reaction equation

HRID 249279 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][C:6]1[CH:5]=[CH:4][C:3]([O:8][CH3:9])=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 2

HCID 336372-MethylanisoleHCID 67184N-bromobutanimide

Product 1

HCID 6083154-Bromo-1-methoxy-2-methylbenzeneYield 47.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 24 g of 2-methylanisole, 35 g of N-bromosuccinimide and 1.24 g of dibenzoyl peroxide in 150 ml of carbon tetrachloride was heated to boiling under reflux for 12 hours. After cooling the solution was filtered and the filtrate is evaporated. The residue was recrystallized from hexane. There were obtained 18.6 g (47%) of 4-bromo-2-methylanisole as a colorless solid; m.p. 66°-68°.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureAfter cooling the solution
  3. filtrationwas filtered
  4. customthe filtrate is evaporated
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-e726e1f3800646a79b1e16dd269c2994
Source dataset
uspto-grants-1993_05
Patent number
US05214046

Linked notes

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