Water → 1-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-4-hydroxymethylbenzimidazole

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Reaction Steps

To 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-acetoxymethylbenzimidazole (Example 103) (1.45 g, 3.38 mmol) dissolved in methanol (19 mL) and water (1.0 mL) was added K2CO3 (0.40 g). After 30 min. the reaction was concentrated, redissolved in EtOAc, and washed with NaHSO4 (10% soln) and NaCl (sat. aq). The combined washings were dried (Na2SO4), filtered, and concentrated. Recrystallization of the crude product from diethylether:hexane (3:1) yielded white crystals of 1-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-4-hydroxymethylbenzimidazole (1.25 g, 3.24 mmol, 96% yield). M.p. 157-158° C. 1H-NMR (300 MHz, CD2Cl2): δ7.54 (m, 1H, H4′), 7.43 (d, J=7.9 Hz, 1H, H7), 7.30-7.22 (m, 2H, H6,4″), 7.18 (d, J=7.5 Hz, 1H, H5), 7.09 (m, 2H, H3′,5′), 6.82 (m, 2H, H3″,5″), 5.37 (s, 2H, CH2PhF2), 5.06 (d, J=5.4 Hz, 2H, CH2O), 3.51 (t, J=5.4 Hz, 1H, OH).

Provenance & Evidence