1,2-Dibromoethane → HCID 66597559, compound

HRID 1518646Notes

Reaction equation

HRID 1518646 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH2:18][CH2:19]Br>CN(C)C=O>[Br:17][CH2:18][CH2:19][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 66597559HCID 66597559, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-(Hydroxyethyl)phenol (2.7 g, 20.0 mmol) was dissolved in N,N-dimethylformamide (50 mL) and thereto were added potassium carbonate (6.90 g, 50.0 mmol) and 1,2-dibromoethane (15.03 g, 80.0 mmol). After stirring at 80° C. for 6 hours, the reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain 2-[4-(2-bromoethoxy)phenyl]-1-ethanol (750.0 mg).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-4b75e3c6798d4d5193b745c486679475
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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