1,2-Dibromoethane → 1,3-Dibromo-2-(2-bromoethoxy)benzene

HRID 603061Notes

Reaction equation

HRID 603061 reaction equation
[Br:1][CH2:2][CH2:3]Br.[OH-].[Na+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[C:9]=1[OH:15].C(OCC)(=O)C>O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[C:9]=1[O:15][CH2:3][CH2:2][Br:1]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 118472,6-DibromophenolHCID 14798Sodium Hydroxide

Product 1

HCID 292722841,3-Dibromo-2-(2-bromoethoxy)benzeneYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,2-Dibromoethane (5.0 ml, 58 mmol) was added to a solution of sodium hydroxide (2.5 g, 63 mmol) and 2,6-dibromophenol (14.5 g, 57.6 mmol) in 45 ml of water. The mixture was stirred under reflux for 20 hours and then extracted with ether. The combined organic layers was dried over Na2SO4, filtered and concentrated to give colorless oil. Silica gel chromatography, using a gradient of ethyl acetate, in hexanes to afforded 1,3-dibromo-2-(2-bromo-ethoxy)-benzene (11.55 g, 57% yield) as a colorless oil.

Workup

  1. temperatureunder reflux for 20 hours
  2. extractionextracted with ether
  3. dry with materialThe combined organic layers was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give colorless oil

Sources & evidence

ORD record
ord-e14deb98f14a49329f0a8cc62e38be85
Source dataset
uspto-grants-2011_03
Patent number
US07906648B2

Reaction notes

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