Sodium Iodide → HCID 22990124, compound

HRID 1169514Notes

Reaction equation

HRID 1169514 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=1.[CH2:13]([O:15][CH2:16][CH2:17]Br)[CH3:14].[I-].[Na+]>CN(C=O)C.O>[Br:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][CH2:14][CH2:13][O:15][CH2:16][CH3:17])=[C:6]([CH3:12])[CH:5]=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

To 60% sodium hydride (4.4 g) suspended in DMF (50 ml) was added dropwise under ice cooling a solution of 4-bromo-2,6-dimethylphenol (20 g) in DMF (100 ml). After stirring at room temperature for 2 hours under a nitrogen atmosphere, bromoethyl ethyl ether (12.3 ml) and sodium iodide (16.4 g) were added thereto, and the resulting mixture was heated overnight at 75° C. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent, and the residue was purified by silica gel chromatography (ethyl acetate/hexane) to obtain 5-bromo-2-(2-ethoxyethoxy)-1,3-dimethylbenzene (24.1 g) as a colorless oil.

Workup

  1. temperaturethe resulting mixture was heated overnight at 75° C
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous saturated solution of sodium chloride, and was dried with anhydrous magnesium sulfate
  5. customThe resulting organic layer was evaporated under reduced pressure
  6. customto remove the solvent
  7. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8377a52a93f74f36b52ab738aca24e08
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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