Hydrochloric Acid → HCID 22379664, compound

Participants

Reaction Steps

2-Chloro-5-nitro-pyridine (60 grams, 0.38 mol) and 4-iodo-phenol (83.5 grams, 0.38 mol), 50% aqueous sodium hydroxide (475 mL) and toluene (475 mL) were added to a flask and stirred at room temperature for 2 hours. The reaction mixture was cooled to 0° C. and concentrated hydrochloric acid was added to adjust the pH to two. The aqueous layer was separated from the toluene layer and extracted with diethyl ether (3×400 mL). The diethyl ether and toluene solution were combined and washed with 1M sodium hydroxide (2×300 mL). The organic layer was concentrated under vacuum to yield 96.5 grams of crude product. This material was recrystallized from hexanes and ethyl acetate to provide 85.3 grams (66%) of the title compound. MS m/z: ESI+ 343.0 (M+H)+.

Provenance & Evidence