Acetic Acid → HCID 178423882, compound

Participants

Reaction Steps

A mixture of 2-iodo-4-(5-methylthiophen-2-yl)-1-trityl-1H-imidazole 2 (2.57 g, 4.83 mmol) and AcOH (3 mL) in MeOH (120 mL) was heated under reflux (2 h). The mixture was allowed to cool to room temperature and then concentrated to give a residue. The residue was taken up in toluene and concentrated to five a residue. The residue was diluted with CH2Cl2, H2O, saturated aqueous NaHCO3 and the organic phase was separated. The aqueous phase was re-extracted (CH2Cl2) and the combined organics were washed (saturated aqueous NaCl), dried (MgSO4), filtered and concentrated to give a residue. The residue was purified by flash chromatography (EtOAc/hexanes 15:85 then 30:70 then 40:60) to give 2-iodo-4-(5-methylthiophen-2-yl)-1H-imidazole 3 (1.2 g, 86%) as a colourless solid. 1H NMR (CDCl3, 400 MHz) □ 2.48 (d, J=1.0 Hz, 3H), 6.65-6.68 (m, 1H), 7.03 (d, J=3.5 Hz 1H), 7.14 (s, 1H).

Provenance & Evidence