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

HRID 338548Notes

Reaction equation

HRID 338548 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Br[CH2:16][CH2:17][O:18][CH3:19]>CN(C)C=O.O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][CH2:17][O:18][CH3:19])=[CH:10][CH:9]=1

Participants

6

Reactant 3

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

Product 1

HCID 140261831-Bromo-4-(2-methoxyethoxy)benzeneYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (2.4 g, 17.3 mmol) was suspended in N,N-dimethyl formamide (15 mL). 4-bromophenol (1.00 g, 5.78 mmol) and 1-bromo-2-methoxyethane (0.964 g, 6.94 mmol) were added into the reaction sequentially and the resulting mixture was stirred at 60° C. for 17 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (50 mL) dried over sodium sulfate and evaporated to give the title compound (1.3 g, 99%) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d1c9704d52ab4f4b899ab7ddb15ee621
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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