4'-Hydroxyacetophenone → 1-(4-(2-Bromoethoxy)phenyl)ethanone

HRID 1968496Notes

Reaction equation

HRID 1968496 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH2:18][CH2:19]Br>CN(C=O)C>[Br:17][CH2:18][CH2:19][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 234408111-(4-(2-Bromoethoxy)phenyl)ethanoneYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-hydroxyphenyl)ethanone (8.2 g, 60.2 mmol), potassium carbonate (15.2 g, 110.1 mmol), and KI (1.0 g, 6.0 mmol) in 100 DMF was stirred for 5 min, then 1,2-dibromoethane (60 ml, 696.2 mmol)was added. The mixture was stirred overnight, evaporated, diluted with EtAc/Hexane (1:1), washed with 0.1 M HCl/NaCl (conc), dried over MgSO4, filtered, evaporated and purified by SiO2 chrmatography eluted with EtAc/Hexane (1:3 to 2:3) to afford 12.41 g (85.2%) of the title compound. 1H NMR (CDCl3) 7.87 (ddd, 2H, J=2.8, 4.9, 9.7 Hz), 6.88 (ddd, 2H, J=2.8, 4.9, 9.6 Hz), 4.29 (t, 2H, J=6.2 Hz), 3.59 (t, 2H, J=6.2 Hz); 13C NMR 196.88, 162.11, 131.15, 130.54, 113.80, 68.06, 29.50, 26.62; MS m/z+ 264.80 (M+Na), 266.80 (M+2+Na).

Workup

  1. customevaporated
  2. additiondiluted with EtAc/Hexane (1:1)
  3. washwashed with 0.1 M HCl/NaCl (conc)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by SiO2 chrmatography
  8. washeluted with EtAc/Hexane (1:3 to 2:3)

Sources & evidence

ORD record
ord-2f83ad842bac4e43a3c0efc5e901f1bf
Source dataset
uspto-grants-2013_04
Patent number
US08426402B2

Reaction notes

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