1,2-Dibromoethane → HCID 86724059, compound

HRID 1519139Notes

Reaction equation

HRID 1519139 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].[OH-].[Na+].[Br:12][CH2:13][CH2:14]Br>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH2:14][CH2:13][Br:12]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 132842722-Bromo-5-chlorophenol

Product 1

HCID 86724059HCID 86724059, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2-bromo-5-chloro-phenol (2.58 g, 12.44 mmol) in water (8 mL) was added sodium hydroxide (995 mg, 24.88 mmol) and the solution heated to reflux for 1 h and then allowed to cool to room temperature. 1,2-dibromoethane (4.67 g, 24.88 mmol) was added and the mixture heated at reflux for 25 h. The solution was allowed to cool to room temperature and partitioned between EtAOc and water. The aqueous was washed with saturated sodium hydrogen carbonate, water and brine and then dried (MgSO4) and concentrated. Material was purified using an ISCO (0-5% EtOAc/hexanes) to afford 1-bromo-2-(2-bromoethoxy)-4-chlorobenzene as a white solid (1.30 g, 33%). 1H NMR (500 MHz, d6-DMSO) δ 7.62 (1H, d), 7.26 (1H, s), 7.02 (1H, d), 4.46 (2H, t), 3.83 (2H, t).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 1 h
  3. temperaturethe mixture heated
  4. temperatureat reflux for 25 h
  5. temperatureto cool to room temperature
  6. custompartitioned between EtAOc and water
  7. washThe aqueous was washed with saturated sodium hydrogen carbonate, water and brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customMaterial was purified

Sources & evidence

ORD record
ord-288fc5e7c03c493e931292b3d3a14c35
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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