Methyl iodide → 1-Bromo-2-methoxy-3-nitrobenzene

HRID 629192Notes

Reaction equation

HRID 629192 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135454532-Bromo-6-nitrophenol

Product 1

HCID 225057131-Bromo-2-methoxy-3-nitrobenzeneYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-6-nitrophenol (5.0 g, 22.9 mmol) was dissolved in DMF (3 mL), potassium carbonate (4.75 g, 34.4 mmol) was added and the reaction was stirred for 30 minutes. Next iodomethane (2.15 mL, 34.4 mmol) was added and the reaction was stirred overnight. The crude reaction was filtered, diluted with ethyl acetate and washed with brine (twice) and water (twice). The organic layer was dried over sodium sulfate, filtered and concentrated to provide 1-bromo-2-methoxy-3-nitrobenzene (5.12 g, 96%). LC retention time 0.92 [J].

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe crude reaction
  3. filtrationwas filtered
  4. additiondiluted with ethyl acetate
  5. washwashed with brine (twice) and water (twice)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cb323723b0c04eb8bfe056acd9693d7e
Source dataset
uspto-grants-2016_04
Patent number
US09315494B2

Reaction notes

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