Sulfuric Acid → (4-Fluoro-3-iodophenyl)methanol

Temperature

60 °C

The product from Example 12A (7.0 g, 50 mmol) in water (100 mL) at 0° C. was treated slowly with concentrated sulfuric acid (30 mL) at a rate to maintain the temperature below 10° C. and then treated dropwise with an aqueous solution of sodiumnitrite (3.45 g, 50 mmol). This solution was then added to a solution of potassium iodide (8.13 g, 50 mmol) in water (15 mL), heated at 60° C. for 2 hours, cooled and extracted with methylene chloride. The methylene chloride layer was washed with 10% sodiumhydroxide, washed with 1 M sodium thiosulfate, washed with 10% hydrochloric acid, washed with aqueous sodium bicarbonate, dried (sodium sulfate), filtered and concentrated. The residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3) to provide 6.4 g of the title compound. 1H NMR (300 MHz, CDCl3) δ 1.69 (t, 1H), 4.66 (d, 2H), 7.05 (t, 1H), 7.60 (d, 1H), 7.78 (dd, 1H).

1. temperatureto maintain the temperature below 10° C.
2. temperaturecooled
3. extractionextracted with methylene chloride
4. washThe methylene chloride layer was washed with 10% sodiumhydroxide
5. washwashed with 1 M sodium thiosulfate
6. washwashed with 10% hydrochloric acid
7. washwashed with aqueous sodium bicarbonate
8. dry with materialdried (sodium sulfate)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by flash chromatography over silica gel (ethyl acetate/hexane 7:3)

ORD record

ord-7e14513726324793ab20b38332357413

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06538004B2