4-Bromoaniline → HCID 68872521, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromoaniline (8.6 g, 50 mmol) in MeOH (100 mL) was added ethyl glyoxalate (12 mL, 60 mmol, 50% in toluene) and the resulting mixture heated at reflux for 3.5 h. The mixture was then concentrated in vacuo and the resulting residue reconstituted in anhydrous ethanol (100 mL) and treated with tosylmethyl isocyanide (14.6 g, 75 mmol) and potassium carbonate (13.8 g, 100 mmol). The resulting mixture was heated at 65° C. for 4 h, then cooled to rt and poured to water (500 mL) and the resulting solid collected by filtration. The crude material thus isolated was crystallized from ethyl acetate/hexane to give pure 3-(4-bromophenyl)-3H-imidazole-4-carboxylic acid ethyl ester (4). MS (ES+): m/z 295/297 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=1.27 (t, J=7.1 Hz, 3H), 4.22 (q, J=7.1 Hz, 2H), 7.22 (d, J=8.7 Hz, 2H), 7.61 (d, J=8.7 Hz, 2H), 7.65 (d, J=0.9 Hz, 1H) and 7.85 (d, J=0.9 Hz, 1H).

Provenance & Evidence