Hydrochloric Acid → 5-Fluoro-4-iodopyridin-2-ol

Concentrated HCl (50 mL) was added to a mixture of 2,5-difluoro-4-iodopyridine (2.0 g, 8.3 mmol) in 1,4-dioxane (350 mL) and water (100 mL). The mixture was heated to reflux and stirred at this temperature overnight. The reaction was concentrated to dryness and the residue was triturated in water (20 mL). The solids were collected via filtration and washed with water (2×30 mL) and hexanes (3×30 mL). The solid was dried under vacuum to afford the title compound as a yellow solid (1.0 g, 50%). MS (LCMS) m/z 240.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.02 (d, J=5.07 Hz, 1H) 7.68 (d, J=2.34 Hz, 1H) 11.50 (br. s., 1H).

1. temperatureThe mixture was heated
2. temperatureto reflux
3. concentrationThe reaction was concentrated to dryness
4. customthe residue was triturated in water (20 mL)
5. filtrationThe solids were collected via filtration
6. washwashed with water (2×30 mL) and hexanes (3×30 mL)
7. customThe solid was dried under vacuum

ORD record

ord-b3f385d3954c46d789eb31074f249c32

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08624034B2