Methyl iodide → 2-Bromo-3-methoxybenzaldehyde

HRID 1810485Notes

Reaction equation

HRID 1810485 reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11](=O)([O-])[O-].[K+].[K+].IC>O.CCOC(C)=O>[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 37146742-Bromo-3-hydroxybenzaldehyde

Product 1

HCID 118102632-Bromo-3-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-3-hydroxybenzaldehyde (0.5 g, 2.4 mmol) was added potassium carbonate (0.77 g, 5.6 mmol), and the mixture was stirred for 5 minutes. Iodomethane (0.17 mL, 2.7 mmol) was added, and the reaction was stirred at room temperature for 2 hours. The mixture was diluted with H2O (30 mL) and EtOAc (30 mL), and the organic layer was washed with 1N aqueous NaOH, then brine, dried over Na2SO4, decanted, and concentrated. The residue was purified by silica gel chromatography (0-60% EtOAc in hexanes) to give the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. washthe organic layer was washed with 1N aqueous NaOH
  3. dry with materialbrine, dried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d85383ad4d284a1dafd7e6d8f454980a
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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