2-Chlorophenol → 1-(2-bromoethoxy)-2-chlorobenzene

HRID 1760924Notes

Reaction equation

HRID 1760924 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9](Br)[CH2:10][Br:11].[OH-].[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][Br:11]

Participants

4

Reactant 3

HCID 72452-ChlorophenolHCID 78391,2-DibromoethaneHCID 14798Sodium Hydroxide

Product 1

HCID 23842071-(2-bromoethoxy)-2-chlorobenzene

Conditions

Temperature
100 °C

Procedure

22.4 ml (0.2 mole) of 2-chlorophenol and 34.6 ml (0.4 mole) of ethylene dibromide are mixed and heated at 100° C. The mixture is stirred vigourously with 125 ml 1.6N NaOH, continued heat and stirred till the pH value to 7. Upon cooling, after filtrating the extracted solids, the mixed solution's organic layer is extracted with chloroform and rinsing the extracted solids with NaCl and MgSO4. The generated product is filled into silica gel chromatography columns. The mixture solution of Hexane and Ethylacetate was used as the eluent solution. Upon purification, until white crystallization 2(2-chlorophenoxy)ethylbromide is obtained.

Workup

  1. temperaturecontinued heat
  2. temperatureUpon cooling
  3. filtrationafter filtrating the extracted solids
  4. extractionthe mixed solution's organic layer is extracted with chloroform
  5. washrinsing the extracted solids with NaCl and MgSO4
  6. additionThe generated product is filled into silica gel chromatography columns
  7. customUpon purification
  8. customuntil white crystallization 2(2-chlorophenoxy)ethylbromide
  9. customis obtained

Sources & evidence

ORD record
ord-3d0593c888f34fdfbfd7ef8ebd7d00dc
Source dataset
uspto-grants-2005_01
Patent number
US06846826B2

Reaction notes

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