2-Methylimidazole → 1-(2-fluoro-4-nitrophenyl)-2-methyl-1H-imidazole

2-Methylimidazole (9.02 g, 0.11 M) and N,N-diisopropylethylamine (32.2 g, 0.25 M) were dissolved in acetonitrile (160 ml), and 3,4-difluoronitrobenzene (15.9 g, 0.1 M) added. The mixture was stirred and heated to reflux under nitrogen for 24 hours. Solvent was evaporated, the residue dissolved in ethyl acetate (300 ml), washed with water (150 ml), brine (150 ml), and dried (magnesium sulfate). The residue was recrystallised from a mixture of ethyl acetate (25 ml) and cyclohexane (150 ml) with the addition of charcoal to give the title compound (11.5 g), mp 106-107°. NMR(DMSO-d6) δ: 2.25 (s, 3H), 7.00 (d, 1H); 7.35 (t, 1H); 7.87 (t, 1H); 8.23 (dd, 1H); 8.43 (dd, 1H). MS (ESP): 222 (MH+) for C10H8FN3O 2

1. temperatureheated
2. temperatureto reflux under nitrogen for 24 hours
3. customSolvent was evaporated
4. dissolutionthe residue dissolved in ethyl acetate (300 ml)
5. washwashed with water (150 ml), brine (150 ml)
6. dry with materialdried (magnesium sulfate)
7. customThe residue was recrystallised from a mixture of ethyl acetate (25 ml) and cyclohexane (150 ml) with the addition of charcoal

ORD record

ord-dafa3cd2cd104e68874d13cacd9b1373

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06734200B1