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

HRID 1167128Notes

Reaction equation

HRID 1167128 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-methyl-3-hydroxy-2-butanone (40 g, 0.392 mol) in anhydrous dichloromethane (2.2 1) 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).

Workup

  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)

Sources & evidence

ORD record
ord-404ad5e091c94e7b9a50dedd1870adbd
Source dataset
uspto-grants-2003_09
Patent number
US06617326B2

Reaction notes

Loading…