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

HRID 586256

反応式

HRID 586256 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d4faf13182bc47a9b71c733c36280686
出典データセット
uspto-grants-2005_08
特許番号
US06936608B2

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