Potassium Iodide → 2-Fluoro-4-hydroxybenzaldehyde

Temperature

40 °C

2-Fluoro-4-methoxy-benzaldehyde (1 g, 6.49 mmol) was added to a suspension of anhydrous potassium iodide (2.15 g, 13 mmol) and aluminum trichloride (1.04 g, 7.8 mmol) in anhydrous toluene (10 mL), and the mixture was stirred at 40° C. for 3 hours. Aluminum trichloride (2.15 g, 13 mmol) and anhydrous potassium iodide (0.86 g, 6.49 mmol) were added, and the mixture was stirred for 3 hours. The mixture was diluted with water (10 mL) and extracted with ethyl acetate (5×20 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 4:1) to give 2-fluoro-4-hydroxy-benzaldehyde as a white solid (260 mg, 29%). 1H NMR (200 MHz, Acetone-d6): δ 10.08 (s, 1H), 9.77 (b, 1H), 7.69 (t, 1H, J=8.4), 6.78 (dd, 1H, J=8.8, 2.6), 6.65 (dd, 1H, J=12.5, 2.2)ppm.

1. stirringthe mixture was stirred for 3 hours
2. extractionextracted with ethyl acetate (5×20 mL)
3. dry with materialThe combined organic layers were dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated under vacuum
6. customThe residue was purified by silica gel chromatography (silica gel, hexanes/ethyl acetate 4:1)

ORD record

ord-b0f443139d904a31b57a0d63f772bb70

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192982B2