Methyl iodide → Methyl 5-bromo-2-methyl-3-nitrobenzoate

HRID 1616347Notes

Reaction equation

HRID 1616347 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:15](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]

Participants

5

Reactant 3

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

Product 1

HCID 24727998Methyl 5-bromo-2-methyl-3-nitrobenzoateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-bromo-2-methyl-3-nitrobenzoic acid (287 g, 1103 mmol) in DMF (150 mL), sodium carbonate (468 g, 4415 mmol) and methyl iodide (626.63 g, 4415 mmol) were added. Resulting reaction mass was heated at 60° C. for 8 h. On completion, solid precipitated was filtered, residue washed with diethyl ether (5 times). Combined organic layers were dried, concentrated under reduced pressure giving the desired crude compound (302 g, 99%).

Workup

  1. customResulting
  2. customreaction mass
  3. customOn completion, solid precipitated
  4. filtrationwas filtered
  5. washresidue washed with diethyl ether (5 times)
  6. customCombined organic layers were dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9aad4943d32a4da08849fb3fb871156d
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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