Methyl iodide → 2-bromo-4,5-dichloro-1-methyl-1H-imidazole

Temperature

75 °C

A mixture of 2-bromo-4,5-dichloroimidazole (1 g, 4.6 mmol), methyl iodide (346 μL, 5.56 mmol), potassium carbonate (1.27 g, 9.2 mmol) and tetrabutylammonium bromide (148 mg, 0.46 mmol) in acetonitrile (2 mL) was stirred vigorously at 70-80° C. for 1.0 h. After cooling to room temperature, the inorganic salts were filtered off and washed with acetonitrile. The filtrate was evaporated and the residue was purified by flash chromatography (Si) to afford 2-bromo-4,5-dichloro-1-methyl-1H-imidazole as a white solid. LCMS calc.=230.89; found=230.9 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 3.61 (s, 3 H).

1. temperatureAfter cooling to room temperature
2. filtrationthe inorganic salts were filtered off
3. washwashed with acetonitrile
4. customThe filtrate was evaporated
5. customthe residue was purified by flash chromatography (Si)

ORD record

ord-328900b32f154e7dbc118c2b0a1b9471

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735435B2