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

HRID 1162087Notes

Reaction equation

HRID 1162087 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br.[OH-].[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[O:9][CH2:12][CH2:11][Br:10]

Participants

5

Reactant 3

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

Product 1

HCID 292722841,3-Dibromo-2-(2-bromoethoxy)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,6-dibromophenol (10.2 g, 40 mmol), 1,2-dibromoethane (7.6 g, 40 mmol) and NaOH (1.76 g, 44 mmol) in water was heated at reflux overnight under stirring. The mixture was cooled, extracted with diethyl ether (2×100 mL), the extract washed with aqueous NaOH, brine, dried (MgSO4) and concentrated to give the product as a pale yellow oil. Yield: 10.0 g (70%). 1H NMR (400 MHz, CDCl3) δ 3.73 (t, 2H), 4.31 (t, 2H), 6.88 (t, 1H), 7.50 (d, 2H). *Previously reported in Tetrahedron Lett. 1998, 39, 2219-2222.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. extractionextracted with diethyl ether (2×100 mL)
  5. washthe extract washed with aqueous NaOH, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d78c5096b8d1437daaa36b504500f126
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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