Potassium Iodide → HCID 86639415, compound

Participants

Reaction Steps

To a solution of 5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2,6-dipropylphenoxy)-2-nitrobenzaldehyde (100 mg, 0.186 mmol) in dioxane/water (2:1, 1.7 mL), iron powder (26 mg, 0.465 mmol) and acetic acid (290 μL) were added sequentially under ice-cold conditions, and the resultant mixture was stirred at room temperature overnight. After completion of the reaction, water and a saturated aqueous solution of sodium hydrogen carbonate were added under ice-cold conditions, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. A solution of the obtained crude product (98 mg) in acetonitrile (0.744 mL) was added with p-toluene sulfonic acid monohydrate (106 mg, 0.558 mmol), added with a mixed aqueous solution (water 100 μL) of sodium nitrite (26 mg, 0.372 mmol) and potassium iodide (77 mg, 0.465 mmol) under ice-cold conditions, and stirred at the same temperature for 5 minutes. Subsequently, the resultant mixture was stirred at room temperature overnight. The reaction solution was added with an aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and (2-iodo-5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2,6-dipropylphenoxy) benzaldehyde (8.0 mg, yield 7.0%) was obtained as a yellow oil.

Provenance & Evidence