3-Hydroxy-3-methyl-2-butanone → 1,1-Dibromo-3-hydroxy-3-methylbutan-2-one

HRID 586256

Reaktionsgleichung

Reaktionsgleichung von HRID 586256
[CH3:1][C:2]([OH:7])([CH3:6])[C:3](=[O:5])[CH3:4].[Br-:8].[Br-:9].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:8][CH:4]([Br:9])[C:3](=[O:5])[C:2]([OH:7])([CH3:6])[CH3:1]

Komponenten

4

Edukt 2

HCID 82613-Hydroxy-3-methyl-2-butanoneHCID 21124087Pyridiniumtribromide

Produkt 1

HCID 114368661,1-Dibromo-3-hydroxy-3-methylbutan-2-oneAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-methyl-3-hydroxy-2-butanone (40 g, 0.392 mol) in anhydrous dichloromethane (2.2 l) under nitrogen was added solid pyridinium tribromide (250.4 g, 0.784 mol) in portions and the mixture was stirred at room temperature for 14 h. The mixture was then washed with dilute aqueous sodium hydrogensulfite (500 ml), then saturated aqueous NaCl (500 ml), dried (Na2SO4), and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, CH2Cl2) to afford 31.4 g (31%) of the title compound as a colourless oil: 1H NMR (360 MHz, CDCl3) δ 1.54 (6H, s), 2.45 (1H, br s), 6.62 (1H, s).

Aufarbeitung

  1. washThe mixture was then washed with dilute aqueous sodium hydrogensulfite (500 ml)
  2. dry with materialsaturated aqueous NaCl (500 ml), dried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash chromatography (silica gel, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d4faf13182bc47a9b71c733c36280686
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936608B2

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