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

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).

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)

ORD record

ord-d4faf13182bc47a9b71c733c36280686

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936608B2