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

HRID 2208681Notes

Reaction equation

HRID 2208681 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 119%

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 compound (302 g, 99%) which was used for further reaction.

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-878164394f97489d80a3f9fe3f7903b7
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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