Methyl iodide → 2-Bromo-1,3-dimethoxy-5-(1-methoxyethyl)benzene

HRID 41249Notes

Reaction equation

HRID 41249 reaction equation
O1CCC[CH2:2]1.[Br:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH:15]([OH:17])[CH3:16])=[CH:9][C:8]=1[O:18][CH3:19].[H-].[Na+].IC>O>[Br:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH:15]([O:17][CH3:2])[CH3:16])=[CH:9][C:8]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 582234841-(4-Bromo-3,5-dimethoxyphenyl)ethanol

Product 1

HCID 582234192-Bromo-1,3-dimethoxy-5-(1-methoxyethyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran (100 mL) solution of 1-(4-bromo-3,5-dimethoxyphenyl)ethanol (7.24 g, 27.7 mmol) was added sodium hydride (1.33 g, 33.2 mmol) at 0° C., and the mixture was stirred for 10 minutes. To the mixture was added dropwise iodomethane (1.90 mL, 30.5 mmol), and the mixture was stirred at room temperature for one hour. After the reaction was completed, water was added to the reaction mixture while cooling on ice, which was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 10/1 then 1/4) to obtain the title compound (7.39 g, 26.9 mmol).

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. temperaturewhile cooling on ice, which
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-9661cd9f131b4feca1184662d0f3fc1a
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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