p-Bromoacetophenone → 1-(4-(2-(Diethylamino)ethoxy)phenyl)ethanone

HRID 1787491Notes

Reaction equation

HRID 1787491 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)=[O:3].[CH3:11][CH2:12][N:13]([CH2:16][CH2:17][OH:18])[CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu].[Cu]I>[CH2:12]([N:13]([CH2:14][CH3:15])[CH2:16][CH2:17][O:18][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1)[CH3:11]

Participants

7

Reactant 3

HCID 7466p-BromoacetophenoneHCID 7497DiethylethanolamineHCID 11430Potassium Carbonate

Product 1

HCID 268511-(4-(2-(Diethylamino)ethoxy)phenyl)ethanoneYield 82.4%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-bromoacetophenone (5 g, 25 mmol), the diethylaminoethanol (3.5 g, 38 mmol), K2CO3 (2 g), copper powder (0.5 g) and copper(I) iodide (2.5 g) in DMSO (30 ml) was heated at 120° C. until TLC showed consumption of the starting material. After cooling to RT, the mixture was poured onto aqueous NH3 (28%, 100 ml), extracted with CH2Cl2 (3×100 ml). The combined organic extracts were dried (Na2SO4), filtered and the CH2Cl2 distilled in vacuo. The crude product was purified by column chromatography on silica gel, eluting with EtOAc-MeOH (95:5) to furnish the pure compound (4.85 g, 82%).

Workup

  1. customconsumption of the starting material
  2. additionthe mixture was poured onto aqueous NH3 (28%, 100 ml)
  3. extractionextracted with CH2Cl2 (3×100 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. distillationthe CH2Cl2 distilled in vacuo
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with EtOAc-MeOH (95:5)

Sources & evidence

ORD record
ord-20230e3124e1449eb11dc5597d164d00
Source dataset
uspto-grants-2009_03
Patent number
US07511047B2

Reaction notes

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