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

HRID 901411Notes

Reaction equation

HRID 901411 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-b089f108ec334081bf018e2d28244f29
Source dataset
uspto-grants-2008_04
Patent number
US07361763B2

Reaction notes

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