Bromine → 1-Bromo-2,4-dimethoxy-5-nitrobenzene

HRID 990847Notes

Reaction equation

HRID 990847 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[Br:14]Br.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:14][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 786332,4-Dimethoxy-1-nitrobenzeneHCID 23665763Sodium Bisulfite

Product 1

HCID 185436101-Bromo-2,4-dimethoxy-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of 2,4-dimethoxy-nitrobenzene (0.50 g) in chloroform (3 mL) is added dropwise a solution of bromine (0.23 g) in chloroform (1 mL) and the mixture is allowed to stir at room temperature for approximately 15 hours. Additional bromine (0.15 g) in chloroform (1 mL) is added and the reaction is stirred for an additional 4 hours. The mixture is then poured onto 5% aqueous sodium bisulfite and then extracted with chloroform. Pooled organic extracts are then washed successively with 5% aqueous sodium bisulfite then saturated sodium chloride, and then dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure and recrystallization of the residue from toluene provides the desired product as a yellow solid.

Workup

  1. stirringthe reaction is stirred for an additional 4 hours
  2. extractionextracted with chloroform
  3. washPooled organic extracts are then washed successively with 5% aqueous sodium bisulfite
  4. dry with materialsaturated sodium chloride, and then dried over anhydrous sodium sulfate
  5. customRemoval of the solvent
  6. customunder reduced pressure and recrystallization of the residue from toluene

Sources & evidence

ORD record
ord-eed28ce218d145899945b2d03644aa70
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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