Methyl iodide → 5-Bromo-1,2-dimethyl-3-nitrobenzene

HRID 2208700Notes

Reaction equation

HRID 2208700 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](O)=O.C(=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[CH3:7][C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]=1[CH3:11]

Participants

5

Reactant 3

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

Product 1

HCID 123818655-Bromo-1,2-dimethyl-3-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To stirred solution of 5-bromo-2-methyl-3-nitrobenzoic acid, prepared analogously to above, (287 g, 1103 mmol) in DMF (150 mL), sodium carbonate (468 g, 4415 mmol) and methyl iodide (626.6 g, 4415 mmol) were added. Resulting mixture was heated at 60° C. for 8 h. On completion, solid was remove by filtration, and 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-nitrobenzene (302 g, 99%).

Workup

  1. customResulting mixture
  2. customOn completion, solid was remove 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-9104854ee5da4a6eb6955f0e39a2cc11
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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