Water → 4-bromo-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole

Participants

Reaction Conditions

Reaction Steps

Into a 250 mL round bottomed flask charged with 4-bromo-6-nitro-1H-benzo[d]imidazole (5 g, 20.66 mmol) in N,N-Dimethylformamide (DMF) (100 mL) was added 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (7.84 g, 31.0 mmol) and potassium carbonate (8.57 g, 62.0 mmol). The resulting reaction mixture was stirred 1 h at 60° C., cooled to room temperature and poured into water, extracted with ethyl acetate, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified on a silica gel cartridge and eluted with a gradient of 0% ethyl acetate/hexanes to 80% over 10 column volumes. The expected compound was collected and evaporated to yield 4-bromo-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole (2.58 g, 6.23 mmol, 30.2% yield) as a tan solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.47 (s, 3H) 5.52 (s, 2H) 7.02 (d, J=7.58 Hz, 1H) 7.27-7.37 (m, 1H) 7.72 (d, J=8.08 Hz, 1H) 8.12 (s, 1H) 8.25 (d, J=2.02 Hz, 1H) 8.48 (d, 1H); LC/MS: MS (ES+) m/e 415 [M+H]+.

Provenance & Evidence