Water → HCID 58203950, compound

HRID 1190719Notes

Reaction equation

HRID 1190719 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC.O.[Br:24][CH2:25][CH2:26]Br>>[Br:24][CH2:25][CH2:26][O:11][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[C:8](=[O:10])[CH3:9]

Participants

6

Reactant 5

HCID 962WaterHCID 6569Methyl Ethyl KetoneHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 959922-Acetyl-4-fluorophenol

Product 1

HCID 58203950HCID 58203950, compoundYield 21.9%

Procedure

Dissolved 1-(5-fluoro-2-hydroxyphenyl)ethanone (10.0 g, 64.9 mmol) in 18 mL 1,2-Dibromoethane and added Potassium carbonate (18.8 g, 136 mmol) and 100 mL 2-Butanone. Heated the reaction mixture to reflux and allowed to stir overnight under nitrogen. Reaction was complete by LCMS. Diluted reaction mixture with water and extracted the product with ethyl acetate. Concentrated in vacuo and purified by flash chromatography (0 to 30% ethyl acetate/heptanes) to give 3.71 g (21.9% yield) of 1-(2-(2-bromoethoxy)-5-fluorophenyl)ethanone.

Workup

  1. temperatureHeated the reaction mixture
  2. temperatureto reflux
  3. customReaction
  4. additionDiluted
  5. extractionextracted the product with ethyl acetate
  6. concentrationConcentrated in vacuo
  7. custompurified by flash chromatography (0 to 30% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-a92ae15ff7d54ac99e4f87fd9fb8654b
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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