Bromotrimethylsilane → Tert-butyl 2-hydroxy-3-methoxy-6-[({4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]benzoate

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Reaction Steps

After trimethylsilyl bromide (55 μl, 0.414 mmol) was added to a solution of tert-butyl 3-methoxy-2-(methoxymethoxy)-6-[({4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]benzoate (180 mg, 0.344 mmol) obtained in Example (51-1) in dichloromethane (4.0 ml), the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into an aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=2/1) to give tert-butyl 2-hydroxy-3-methoxy-6-[({4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]benzoate (146 mg, yield: 89%).

Provenance & Evidence