N-bromobutanimide → 2-(Bromomethyl)-1-methoxy-3-methylbenzene

HRID 1357027Notes

Reaction equation

HRID 1357027 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:10][O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH2:1][Br:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 762692,3-Dimethylanisole

Product 1

HCID 103532222-(Bromomethyl)-1-methoxy-3-methylbenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

0.50 g (3.68 mmol) of 2,3-dimethylanisole was dissolve in 10 ml of carbon tetrachloride. The resultant solution was then added with 0.72 g (4.04 mmol) of N-bromosuccinimide, and the obtained solution was subjected to irradiation of light (Infrared lamp 375WR manufactured by Toshiba) for 45 min. at the reflux temperature. The solution was then cooled down, and the temperature thereof was maintained at a room temperature to cause the precipitation. The precipitated succinimide was separated by filtration, and the obtained filtrate was condensed under reduced pressure to produce a crude product of 2-methoxy-6-methylbenzyl bromide.

Workup

  1. customthe obtained solution was subjected to irradiation of light (Infrared lamp 375WR manufactured by Toshiba) for 45 min. at the reflux temperature
  2. temperatureThe solution was then cooled down
  3. customthe precipitation
  4. customThe precipitated succinimide was separated by filtration
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-b21b8281ce6f44fd99f17c0ceed44602
Source dataset
uspto-grants-2003_07
Patent number
US06589967B1

Reaction notes

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