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

HRID 2119502Notes

Reaction equation

HRID 2119502 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-7d1b9bf8b593483db4f7a8c0184c0e37
Source dataset
uspto-grants-2004_02
Patent number
US06686351B2

Reaction notes

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