Diethyl Sulfate → 4-Bromo-3,5-dimethoxybenzyl ethyl ether

HRID 1454113Notes

Reaction equation

HRID 1454113 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:12][CH3:13].[OH-].[Na+].S(OCC)(O[CH2:20][CH3:21])(=O)=O>C(Cl)C1C=CC=CC=1.C([NH+](CC)CC)C>[CH2:20]([O:7][CH2:6][C:5]1[CH:8]=[C:9]([O:10][CH3:11])[C:2]([Br:1])=[C:3]([O:12][CH3:13])[CH:4]=1)[CH3:21]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 11149289(4-Bromo-3,5-dimethoxyphenyl)methanol

Product 1

HCID 668796444-Bromo-3,5-dimethoxybenzyl ethyl etherYield 99.9%

Reagents, catalysts & solvents 1

HCID 22101882Triethylammonium benzyl chlorideCatalyst

Conditions

Temperature
27.5 °C

Procedure

To a mixture of 4-bromo-3,5-dimethoxybenzylalcohol (44.5 g), triethylammonium benzyl chloride (2.05 g) and 20% aqueous sodium hydroxide solution (288 g) was added diethyl sulfate (41.7 g) under ice-cooling, and the mixture was stirred overnight at 25-30° C. After stirring for 1 hour at 70° C., the mixture was cooled and extracted with toluene. The toluene layer was washed with water and saturated aqueous NaCl solution and dried over magnesium sulfate. The solvent was removed in vacuo to yield 4-bromo-3,5-dimethoxybenzyl ethyl ether (49.5 g) as colorless oil.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 1 hour at 70° C.
  3. temperaturethe mixture was cooled
  4. extractionextracted with toluene
  5. washThe toluene layer was washed with water and saturated aqueous NaCl solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bb768001dc4a44b9801162ba86f8baef
Source dataset
uspto-grants-2009_01
Patent number
US07476758B2

Reaction notes

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