1,1-Dibromoethane → 1-(2-Bromoethoxy)-3,5-dichlorobenzene

HRID 1699012Notes

Reaction equation

HRID 1699012 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([Cl:10])[CH:9]=1.[Br:12][CH:13](Br)[CH3:14]>O.CCOC(C)=O>[Br:12][CH2:13][CH2:14][O:11][C:6]1[CH:5]=[C:4]([Cl:3])[CH:9]=[C:8]([Cl:10])[CH:7]=1

Participants

6

Reactant 3

HCID 112011,1-DibromoethaneHCID 115713,5-DichlorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 222467761-(2-Bromoethoxy)-3,5-dichlorobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of NaOH (2.45 g, 61.3 mmol) in water (20 mL) was added 3,5-dichlorophenol (5 g, 30.7 mmol). The solution was heated at reflux for 1 h and was cooled to room temperature. Dibromoethane (11.52 g, 61.3 mmol) was added and the reaction was heated at reflux for 24 h. The cooled solution was diluted with EtOAc and the organic solution was washed sequentially with HCl (1N, 1×), water (1×), and brine (1×). The organic solution was dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (hexanes to 5% EtOAc in hexanes ) provided the title compound (3.79 9). 1H NMR (400 MHz, CDCl3) δ6.98 (m, 1H), 6.82 (m, 2H), 4.25 (t, 2H), 3.61 (t, 2H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 1 h
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 24 h
  5. washthe organic solution was washed sequentially with HCl (1N, 1×), water (1×), and brine (1×)
  6. dry with materialThe organic solution was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (hexanes to 5% EtOAc in hexanes )

Sources & evidence

ORD record
ord-d05545691e1b4353a72d0edf083bbb5f
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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