Hydrochloric Acid → 3-Fluoro-4-hydroxy-5-iodobenzonitrile

Potassium iodide (7.97 g, 48 mmol) was dissolved in 125 ml of DMF with stirring, and 4-cyano-2-fluorophenol (16a; 5.56 g 48 mmol) and chloramine-T in 75 ml of DMF were added dropwise with stirring. The reaction mixture was poured into 650 ml of water, acidified with 6N HCl, and extracted with ethyl acetate. The organic layer was washed with 10% NaHSO3, water and brine and dried over magnesium sulfate. The organic solution was concentrated in vacuo and the yellow solid residue was treated with 200 ml of 1N NaOH solution, filtered through supercel, and the filtrate was acidified with conc. HCl solution. The solid product was filtered, dried, dissolved in ether, and the organic layer was dried over magnesium sulfate. The organic solution was concentrated in vacuo and the residue was recrystallized from ethylene chloride to afford 5.93 g (55.6%) of the title compounds.

1. stirringwith stirring
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with 10% NaHSO3, water and brine
4. dry with materialdried over magnesium sulfate
5. concentrationThe organic solution was concentrated in vacuo
6. additionthe yellow solid residue was treated with 200 ml of 1N NaOH solution
7. filtrationfiltered through supercel
8. filtrationThe solid product was filtered
9. customdried
10. dissolutiondissolved in ether
11. dry with materialthe organic layer was dried over magnesium sulfate
12. concentrationThe organic solution was concentrated in vacuo
13. customthe residue was recrystallized from ethylene chloride

ORD record

ord-a757a5b3453d4d1282436b46e3c69f2d

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05643929