3-Fluoro-3-methylbutan-2-one → 1,1-Dibromo-3-fluoro-3-methyl-2-butanone

To a stirred solution of 3-methyl-3-fluoro-2-butanone (0.1031 g, 0.990 mmol) in anhydrous dichloromethane (5 ml) under nitrogen was added solid pyridinium tribromide (0.7035 g, 1.98 mmol) and the mixture was stirred at room temperature for 18 h. The mixture was then diluted with dichloromethane (5 ml), washed with dilute aqueous sodium hydrogensulfite (10 ml), then saturated aqueous NaCl (10 ml), dried (Na2SO4) and evaporated under low vacuum with no heat. The residue was purified by flash chromatography [silica gel, 5% Et2O/petroleum ether (40-60° C.)] to afford 0.1869 g (72%) of the title compound as a colourless oil: 1H NMR (360 MHz, CDCl3) δ1.65 (6H, d, J 21.5 Hz), 6.51 (1H, d, J 1.5 Hz).

1. washwashed with dilute aqueous sodium hydrogensulfite (10 ml)
2. dry with materialsaturated aqueous NaCl (10 ml), dried (Na2SO4)
3. customevaporated under low vacuum with no heat
4. customThe residue was purified by flash chromatography [silica gel, 5% Et2O/petroleum ether (40-60° C.)]

ORD record

ord-940b48c6d02643959e87e8d7e0ef21b5

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696444B2