4-Bromophenol → 1-Bromo-4-(2-methoxyethoxy)benzene

HRID 1964960Notes

Reaction equation

HRID 1964960 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][O:18][CH3:19]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH2:17][O:18][CH3:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 140261831-Bromo-4-(2-methoxyethoxy)benzeneYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromophenol (646, 5.0 g, 28.9 mmol) in dimethylformamide (15 mL) were added potassium carbonate (4.40 g, 31.8 mmol) and 1-bromo-2-methoxyethane (5.00 g, 36.0 mmol) under an atmosphere of nitrogen. The reaction mixture was stirred at ambient temperature overnight and concentrated under reduced pressure. The residue was slurried in ethyl acetate (50 mL) and filtered. The filtrate was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and filtered. Silica gel column chromatography (0-10% ethyl acetate in hexanes) gave the desired compound as a colorless oil (647, 3.2 g, 48%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationfiltered
  3. washThe filtrate was washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-b7ef1b6e25fe48bbbee6110765f16fd2
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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