Sodium Iodide → 1-Bromo-4-(2-methoxyethoxy)benzene

HRID 1978615Notes

Reaction equation

HRID 1978615 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][CH2:19][O:20][CH3:21]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][CH2:19][O:20][CH3:21])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl ether

Product 1

HCID 140261831-Bromo-4-(2-methoxyethoxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-bromophenol (15 g), sodium iodide (13.0 g) and potassium carbonate (14.4 g) in DMF (200 ml) was added at room temperature 2-chloroethylmethyl ether (9 ml), and the mixture was stirred at 80° C. for 3 days. To the mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give orange oil of 1-bromo-4-(2-methoxyethoxy)benzene (17.44 g).

Workup

  1. extractionthe mixture was extracted with diethylether
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2e002814c224826b6904faf1b693641
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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