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

HRID 2208771Notes

Reaction equation

HRID 2208771 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 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. The resulting reaction mixture was heated at 60° C. for 8 h. On completion, a solid precipitated was filtered, residue washed with diethyl ether (5 times). The combined organic layers were dried, concentrated under reduced pressure giving desired compound (302 g, 99%) which was used as is in subsequent steps.

Workup

  1. additionwere added
  2. customThe resulting reaction mixture
  3. customOn completion, a solid precipitated
  4. filtrationwas filtered
  5. washresidue washed with diethyl ether (5 times)
  6. customThe combined organic layers were dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb7a596c76d44d59a9b6360212bb2e18
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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