Bromotrichloromethane → HCID 57550204, compound

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A stirred solution of methyl {2-{4-[(1-methyl-1H-benzimidazol-2-yl)methyl]-phenyl}-4,5-dihydro-1,3-oxazol-4-yl}carboxylate (1.5 g, 5 mmol) in CH2Cl2 was treated with bromotrichloromethane (1.22 g, 6 mmol) and DBU (0.70 g, 4.6 mol), stirred at room temperature overnight and concentrated in vacuo. The resultant residue was purified by column chromatography (silica, CHCl3:MeOH 1%) to give the title compound in 15% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, CDCl3): 8.2 (s, 1H), 8.06 (d, J=8.0 Hz, 2H), 7.3 (d, J=8.0 Hz, 2H), 7.27 (m, 4H), 4.3 (s, 2H), 3.95 (s, 3H), 3.63 (s, 3H). LCMS (ESI+) 348 (MH+).

Provenance & Evidence