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

HRID 1030671Notes

Reaction equation

HRID 1030671 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-9f7f8941df204d8c917e52a67d15d7f9
Source dataset
uspto-grants-1992_04
Patent number
US05106878

Reaction notes

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