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

HRID 1616383Notes

Reaction equation

HRID 1616383 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) was added sodium carbonate (468 g, 4415 mmol) and methyl iodide (626.63 g, 4415 mmol). The resulting reaction mixture was heated at 60° C. for 8 h. On completion, the precipitated solid was collected by filtration, the residue washed with diethyl ether (5 times). The combined organic layers were dried, concentrated under reduced pressure to give methyl 5-bromo-2-methyl-3-nitrobenzoate (302 g, 99%) which was used directly in the next step.

Workup

  1. customThe resulting reaction mixture
  2. filtrationOn completion, the precipitated solid was collected by filtration
  3. washthe residue washed with diethyl ether (5 times)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c64521602979404aadbdcadc5ba632c6
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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