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

HRID 1781961Notes

Reaction equation

HRID 1781961 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:3]=[C:4]([O:9][CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=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 refluxing solution of 3,5-dimethylanisole (13 g), azoisobutyronitrile (1.6 g) and N-bromosuccinimide (17 g) in carbon tetrachloride (100 ml) was irradiated with light for 6 h. The solution was filtered and the solvent removed in vacuo. The residue was purified by chromatography on silica gel (eluting with 0-5% ethyl acetate--petroleum ether bp=60°-80° C.) to yield 3-bromomethyl-5-methylanisole.

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by chromatography on silica gel (eluting with 0-5% ethyl acetate--petroleum ether bp=60°-80° C.)

Sources & evidence

ORD record
ord-202a9bbb4dca40d0b986898be9ca314e
Source dataset
uspto-grants-1997_05
Patent number
US05633281

Reaction notes

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