4-Iodophenol → HCID 89555388, compound

Participants

Reaction Steps

N,N-dimethylformamide (hereinafter, DMF) (100 mL), potassium carbonate (1.1 g, 7.8 mmol), and methyl 3-(bromomethyl)benzoate (1.2 g, 5.2 mmol) were added to 4-iodophenol (1.2 g, 5.5 mmol), and stirred at room temperature overnight. Ethyl acetate was used as an extraction solvent, and after washing with water, a 1 N sodium hydroxide aqueous solution, and saturated brine, the resultant was dried over magnesium sulfate. The solvent was distilled away under reduced pressure. To the resulting residue (1.9 g, 5.2 mmol), tetrahydrofuran (hereinafter, THF) (10 mL), methanol (10 mL), and a 1 N sodium hydroxide aqueous solution (20 mL) were added, and stirred at room temperature for 4 hours. Ethyl acetate was used as an extraction solvent, and after washing with a 1 N hydrochloric acid aqueous solution and saturated brine, the resultant was dried over magnesium sulfate. The solvent was distilled away under reduced pressure. To the resulting residue, thionyl chloride (20 mL) was added, and stirred at 40° C. for 1 hour. After that, the solvent was distilled away under reduced pressure. To the resulting residue, dichloromethane (10 mL), a 1 N sodium hydroxide aqueous solution (15 mL), and L-proline (1.1 g, 9.2 mmol) were added, and stirred at room temperature overnight. The solvent was distilled away under reduced pressure. The resultant was washed with a 1 N hydrochloric acid aqueous solution and saturated brine, and then dried over magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was washed with a water-acetonitrile mixture solvent, and then dried to thus obtain the title compound.

Provenance & Evidence