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

HRID 2208914Notes

Reaction equation

HRID 2208914 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 crude 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 g, 4415 mmol) were added. The mixture was heated at 60° C. for 8 h, cooled to room temperature. The solid precipitate was filtered and washed with diethyl ether (5 times). The combined organic layers were dried and concentrated under reduced pressure to give the title compound (302 g, 99%) which was used directly.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe solid precipitate was filtered
  3. washwashed with diethyl ether (5 times)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1fb6439a2a2240ed9f84d31c03052b5e
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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