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

4-Methylimidazole (45.1 g, 0.55 M) and N,N-diisopropylethylamine (161 g, 1.25 M) were dissolved in acetonitrile (800 ml), and 3,4-difluoronitrobenzene (79.5 g, 0.5 M) added. The mixture was stirred and heated to reflux under nitrogen for 24 hours. Solvent was evaporated, the residue dissolved in ethyl acetate (800 ml), washed with water (400 ml), brine (200 ml), and dried (magnesium sulfate). The residue was dissolved in toluene (250 ml), treated with charcoal, filtered, and diluted with hot cyclohexane (75 ml) to crystallise 3-fluoro-4-(4-methylimidazol-1-yl)nitrobenzene (64.7 g). NMR (DMSO-d6) δ: 2.18 (s, 3H); 7.29 (s, 1H); 7.92 (t, 1H); 8.07 (s, 1H); 8.18 (dd, 1H); 8.38 (dd, 1H). MS (ESP): 222 (MH+) for C10H8FN3O2

1. temperatureheated
2. temperatureto reflux under nitrogen for 24 hours
3. customSolvent was evaporated
4. dissolutionthe residue dissolved in ethyl acetate (800 ml)
5. washwashed with water (400 ml), brine (200 ml)
6. dry with materialdried (magnesium sulfate)
7. dissolutionThe residue was dissolved in toluene (250 ml)
8. additiontreated with charcoal
9. filtrationfiltered
10. additiondiluted with hot cyclohexane (75 ml)
11. customto crystallise 3-fluoro-4-(4-methylimidazol-1-yl)nitrobenzene (64.7 g)

ORD record

ord-1f04384498314a44b885d55fd9e92e20

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06734200B1