Sodium Iodide → 1-Bromo-3-ethoxy-4-(2-ethoxyethoxy)benzene

HRID 1978741Notes

Reaction equation

HRID 1978741 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH2:10][CH3:11])[CH:3]=1.Br[CH2:13][CH2:14][O:15][CH2:16][CH3:17].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:14][O:15][CH2:16][CH3:17])=[C:4]([O:9][CH2:10][CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 218775414-Bromo-2-ethoxyphenol

Product 1

HCID 219958181-Bromo-3-ethoxy-4-(2-ethoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 4-bromo-2-ethoxyphenol (8 g), bromoethylethyl ether (5 ml), sodium iodide (5.5 g) and potassium carbonate (10.2 g) in DMF (10 ml) was stirred under nitrogen atmosphere at 90° C. overnight. The solvent was evaporated, and to the residue was added water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated, and the residue was distilled under reduced pressure to give 1-bromo-3-ethoxy-4-(2-ethoxyethoxy)benzene (8.1 g) as yellow oil.

Workup

  1. customThe solvent was evaporated
  2. additionto the residue was added water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-634e959b69c5429c9d5a0e10160dfb97
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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