Sodium Iodide → HCID 22990124, compound

HRID 1978739Notes

Reaction equation

HRID 1978739 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][O:16][CH2:17][CH3:18].[I-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:14][CH2:15][O:16][CH2:17][CH3:18])=[C:4]([CH3:10])[CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 169194-Bromo-2,6-dimethylphenolHCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl ether

Product 1

HCID 22990124HCID 22990124, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-bromo-2,6-dimethylphenol (20 g) in DMF (10 ml) was added dropwise to a suspension of 60% sodium hydride (4.4 g) in DMF (50 ml) under ice-cooling, and the mixture was stirred under nitrogen atmosphere at room temperature for 2 hours. To the mixture were added bromoethylethyl ether (12.3 ml) and sodium iodide (16.4 g), and the mixture was stirred at 75° C. overnight. The mixture was poured into water, and 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 5-bromo-2-(2-ethoxyethoxy)-1,3-dimethylbenzene (24.1 g) as colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 75° C. overnight
  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-8bd55ac2a93b4bea9fd744fc3fea06a6
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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