N-bromobutanimide → Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-

HRID 1357034Notes

Reaction equation

HRID 1357034 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH2:1][Br:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 785542-Methyl-3-nitroanisole

Product 1

HCID 186047Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3.0 g (18 mmol) of 2-methyl-3-nitroanisole was dissolved in 500 ml of carbon tetrachloride. The resultant solution was added with 6.4 g (36 mmol) of N-bromosuccinimide, and the mixture was subjected to irradiation of light emitted from an infrared lamp of 375 W (manufactured by Toshiba) for 3 hours at the reflux temperature. The mixture was then cooled to a room temperature. Succinimide precipitated in the mixture was separated by filtration, and the obtained filtrate was condensed under reduced pressure to obtain a crude product of 2-methoxy-6-nitrobenzyl bromide.

Workup

  1. customthe mixture was subjected to irradiation of light
  2. customSuccinimide precipitated in the mixture
  3. customwas separated by filtration
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-657ad06af4cf4870811f8345aeaafe1c
Source dataset
uspto-grants-2003_07
Patent number
US06589967B1

Reaction notes

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