Methyl iodide → Methyl 4-bromo-2,6-diMethylbenzoate

HRID 2427491Notes

Reaction equation

HRID 2427491 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:12])[CH:3]=1.IC.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][O:7][C:6](=[O:8])[C:5]1[C:9]([CH3:11])=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 119590064-Bromo-2,6-dimethylbenzoic acid

Product 1

HCID 23134395Methyl 4-bromo-2,6-diMethylbenzoateYield 102.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromo-2,6-dimethylbenzoic acid (2.81 g, 12.3 mmol) in DMF (30 mL) was added iodomethane (2.30 mL, 36.9 mmol) and potassium carbonate (5.09 g, 36.9 mmol) and reaction was stirred at room temperature for 1.5 hours. The reaction mixture was partitioned between water and ethyl acetate and the organic layer was washed with brine. The solvent was removed under reduced pressure to yield an amber oil (3.06 g). 1H NMR (300 MHz, CDCl3): δ 7.22 (S, 2H), 3.92 (s, 3H), 2.30 (s, 6H).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with brine
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bb732ef129124dca95eed02b4be8a6d9
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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