Methyl iodide → Methyl 2-bromo-5-methoxybenzoate

HRID 2224652Notes

Reaction equation

HRID 2224652 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](=O)(O)[O-].[K+].CI>CN(C)C=O.O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 899062-Bromo-5-methoxybenzoic acidHCID 516893Potassium Bicarbonate

Product 1

HCID 2776849Methyl 2-bromo-5-methoxybenzoateYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-methoxybenzoic acid (15.0 g) in dimethylformamide (100 ml) were added potassium bicarbonate (7.83 g) and methyl iodide (8.12 ml) and the mixture was stirred for 20 hours at room temperature. The reaction mixture was diluted with water and was extracted with a mixture of ethyl acetate and hexane (1/1). The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:1) to give the title compound (16.3 g) having the following physical data.

Workup

  1. extractionwas extracted with a mixture of ethyl acetate and hexane (1/1)
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-0a6e1ef5712a479d82b01e419811db0b
Source dataset
uspto-grants-2008_05
Patent number
US07378428B2

Reaction notes

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