1-Methoxy-4-methyl-2-nitrobenzene → 4-(Bromomethyl)-1-methoxy-2-nitrobenzene

HRID 1370120

Reaction equation

HRID 1370120 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].[Br:13]N1C(=O)CCC1=O>ClCCl.N(C(C)(CC(OC)(C)C)C#N)=NC(C)(CC(C)(OC)C)C#N>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Br:13])=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 670581-Methoxy-4-methyl-2-nitrobenzeneHCID 67184N-bromobutanimide

Product 1

HCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzeneYield 78.2%

Reagents, catalysts & solvents 2

HCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)CatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-3-nitrotoluene (5.02 g) and N-bromosuccinimide (5.51 g) in dichloromethane (50 mL) was added 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (463 mg). The mixture was heated under reflux for 8 hours. The solution was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with n-hexane-ethyl acetate (20:1) to give 4-methoxy-3-nitrobenzyl bromide as a pale yellow powder (5.78 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. washThe solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with n-hexane-ethyl acetate (20:1)

Sources & evidence

ORD record
ord-9b00f5281c724f9a8e1e3bef3a83a71c
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Linked notes

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