Water → 4-Bromo-2-chloro-1-(2-ethoxyethoxy)benzene

HRID 1978623Notes

Reaction equation

HRID 1978623 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][O:19][CH2:20][CH3:21].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][O:19][CH2:20][CH3:21])=[C:4]([Cl:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenolHCID 611412-Bromoethyl ethyl ether

Product 1

HCID 219959534-Bromo-2-chloro-1-(2-ethoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-bromo-2-chlorophenol (15.92 g) and potassium carbonate (15.9 g) in DMF (100 ml) was added at room temperature 2-bromoethylethyl ether (9.51 ml), and the mixture was stirred at 60° C. for 18 hours. To the mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give pale yellow oil of 4-bromo-2-chloro-1-(2-ethoxyethoxy)benzene (21.76 g).

Workup

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

Sources & evidence

ORD record
ord-83e871971d17469ea098740e23d2e6d9
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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