Tetrabutylammonium Fluoride → 3-((4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenol

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Reaction Steps

To a solution of intermediate 217.2 (500 mg, 0.669 mmol) in 5 mL THF at rt, was added TBAF (1M in THF, 0.669 mL, 0.669 mmol). The mixture was stirred at rt for 30 min. The mixture was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was triturated with hexanes (10 mL) to afford 3-((4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenol. To a solution of this product in 5 mL DMF at rt, were added K2CO3 (111 mg, 0.803 mmol) and iodoethane (161 μL, 2.01 mmol). The mixture was stirred at rt for 15 h, then diluted with EtOAc. The organic phase was washed with H2O (2×), sat. Na2SO3 and brine, dried (Na2SO4), filtered through a 1″ pad of silica gel and concentrated to afford 433 mg of Intermediate 217.3 as an off-white solid.

Provenance & Evidence