1,2-Dibromoethane → 1-(4-(2-Bromoethoxy)phenyl)ethanone

HRID 2304692Notes

Reaction equation

HRID 2304692 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[Br:11][CH2:12][CH2:13]Br.C(=O)([O-])[O-:16].[K+].[K+]>CN(C)C=O>[Br:11][CH2:12][CH2:13][O:16][C:6]1[CH:5]=[CH:4][C:3]([C:8](=[O:10])[CH3:9])=[CH:2][CH:7]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 83752'-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 234408111-(4-(2-Bromoethoxy)phenyl)ethanoneYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-(hydroxyphenyl)ethanone (2.72 g, 20.0 mmol), 1,2-dibromoethane (7.676 g, 40.0 mmol), and potassium carbonate (5.52 g, 40 mmol) in dried dimethylformamide (40 mL) was heated at 50° C. overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated, and purified by column chromatography (SiO2, 20-70% ethyl acetate/hexane) to provide the title compound (1.91 g, 39% yield): 1H NMR (CDCl3) 7.95 (t, 2H), 6.95 (t, 2H), 4.36 (t, 2H), 3.67 (t, 2H), 2.57 (s, 3H); ES-MS (m/z) 243 [M+H]+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (SiO2, 20-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9d67ab7491684e2a888f49d926e6baef
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

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