N-bromobutanimide → 1-(Bromomethyl)-3-methoxy-5-methylbenzene

HRID 1833266Notes

Reaction equation

HRID 1833266 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 701263,5-Dimethylanisole

Product 1

HCID 5855341-(Bromomethyl)-3-methoxy-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 3,5-dimethylanisole (1.11 g, 8.15 mmol), N-bromosuccinimide (1.52 g, 8.55 mmol), and 2,2′-bisisobutyronitrile (27 mg, 0.16 mmol) in carbontetrachloride (10 mL) was refluxed for 2 hrs. The reaction mixture was cooled, filtered and concentrated in vacuo to afford 1-bromomethyl-3-methoxy-5-methyl-benzene as a slightly yellow oil (1.66 g). This material was used without further purification: 1H NMR (300 MHz) compatible.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69db10452cc04e5da9eb65efe2ccffb6
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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