Methyl iodide → Methyl 3-bromo-5-nitrobenzoate

HRID 2208688Notes

Reaction equation

HRID 2208688 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5](C)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].IC.[C:17](=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:6]([CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1)[C:7]([O:9][CH3:17])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 137700085-Bromo-2-methyl-3-nitrobenzoic acid

Product 1

HCID 239341Methyl 3-bromo-5-nitrobenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-bromo-2-methyl-3-nitrobenzoic acid (16 g, 61.54 mmol) in DMF (160 mL), iodomethane (35.72 g, 248 mmol) and sodium carbonate (26.28 g, 248 mmol) were added. Resulting reaction mass was stirred at 60° C. for 8 h. On completion, reaction mass was filtered and inorganic solid residue washed with ethyl acetate. Combined filtrates were concentrated under vacuum till dryness. The residue was re-dissolved in ethyl acetate and washed with 5% sodium bicarbonate solution (700 mL) followed by 5M HCl solution (300 mL). Organic layer was finally washed with brine, dried over sodium sulfate and concentrated to afford desired compound (16 g, 95%).

Workup

  1. customResulting
  2. customreaction mass
  3. customOn completion, reaction mass
  4. filtrationwas filtered
  5. washinorganic solid residue washed with ethyl acetate
  6. concentrationCombined filtrates were concentrated under vacuum till dryness
  7. dissolutionThe residue was re-dissolved in ethyl acetate
  8. washwashed with 5% sodium bicarbonate solution (700 mL)
  9. washOrganic layer was finally washed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e8b94381a30044e09c4297b9c40a1266
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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