1-Acetylnaphthalene → 2-Bromo-1-(1-naphthalenyl)ethanone

HRID 386394

Reaktionsgleichung

Reaktionsgleichung von HRID 386394
[C:1]1([C:11](=[O:13])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:14]Br>O1CCOCC1>[Br:14][CH2:12][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:13]

Komponenten

4

Edukt 2

HCID 136631-AcetylnaphthaleneHCID 24408Bromine

Produkt 1

HCID 38305132-Bromo-1-(1-naphthalenyl)ethanoneAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(naphthalen-1-yl)ethanone (500 mg, 2.9 mmol) in dioxane (5 mL) was added to a solution of bromine (510 mg, 3.19 mmol) in dioxane (10 mL), at room temperature, over a period of 30 minutes. The reaction mixture was then stirred at room temperature for 20 minutes and concentrated. The resulting residue was diluted with ether and washed with saturated sodium bicarbonate, water, dried over sodium sulfate and concentrated. Purification by preparative thin layer chromatography (70% DCM/30% hexanes) afforded 2-bromo-1-(naphthalen-1-yl)ethanone (673 mg, 93%).

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe resulting residue was diluted with ether
  3. washwashed with saturated sodium bicarbonate, water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by preparative thin layer chromatography (70% DCM/30% hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-28433479610f4dd89803e5dd0db30856
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372807B2

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