4-Iodophenol → HCID 19261706, compound

Participants

Reaction Conditions

Reaction Steps

A resealable tube was charged with 4-iodophenol 99b (2.50 g, 11.4 mmol), 4-(2-chloroethyl)morpholine hydrochloride (2.14 g, 11.5 mmol), potassium carbonate (7.88 g, 57.0 mmol), and acetonitrile (50 mL). The system was flushed with argon, the tube was sealed, and the mixture stirred at 85° C. for 20 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford a pale orange oil. This oil was purified via column chromatography (eluting with 0-100% ethyl acetate-hexane) to afford 4-[2-(4-iodo-phenoxy)-ethyl]-morpholine 100b as a pale yellow oil. MS (MH+) 334.0; Calculated 333 for C12H16INO2.

Provenance & Evidence