Sodium Carbonate → Methyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

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Reaction Steps

A solution of ethyl [4-(4-bromomethyl-3-isopropyl-phenylethynyl]-benzoate (Intermediate 155, 120.0 mg, 0.31 mmol) and 1-acetylimidazole (36.0 mg, 0.33 mmol) in 5 mL CH3CN was heated at 65° C. for 4 hours and then at 55° C. for 16 hours. The solution was cooled to room temperature, diluted with H2O and made basic by addition of Na2CO3, and extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl, dried (MgSO4), and concentrated under reduced pressure. Column chromatography (1% Et3N in 5% MeOH-EtOAc) afforded 75.0 mg (65%) of the title compound as a colorless solid.

Provenance & Evidence