(1-((2,6-Difluorophenyl)methyl)-4-methylbenzimidazol-2-yl)methan-1-ol → 1H-Benzimidazole, 1-((2,6-difluorophenyl)methyl)-4-methyl-

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Reaction Steps

In this Example, 1-(2,6-difluorobenzyl)-4-methylbenzimidazole (49) was prepared according to Method D. To 1-(2,6-difluorobenzyl)-2-hydroxymethyl-4-methylbenzimidazole (Example 40) (1.82 g, 4.52 mmol) dissolved in 1.5 M H2SO4 (40 mL) was added KMnO4 (1.50 g, 9.49 mmol, 160 M%). After 1 h at room temperature, the reaction mixture was filtered and washed with water. The brown solid was collected, suspended in acetone/methanol and filtered. The filtrate was collected and purified by flash chromatography eluting with 10% MeOH/CH2Cl2 increasing to 50% MeOH/CH2Cl2 to produce 1.42 g (4.70 mmol, 80% yield) of white powder. 1H-NMR (200 MHz, CD2Cl2): δ7.99 (br s, 1H, H2), 7.37 (br d, J=7.9 Hz, 1H, H7), 7.32 (m, 1H, H4″), 7.17 (dd, J=7.3, 7.9 Hz, 1H, H6), 7.03 (d, J=3.2 Hz, 1H, H5), 6.96 (m, 2H, H3″,5″,), 5.40 (s, 2H, CH2PhF2), 2.59 (s, 3H, CH3).

Provenance & Evidence