Nitric Acid → HCID 15544164, compound

A mixture of 1-fluoro-2-(pentafluoro-λ6-sulfanyl)benzene (2.00 g, 9.00 mmol) and sulfuric acid (4 mL) was cooled in an ice bath. Nitric acid (4 mL) was added to the reaction mixture; after 5 minutes, the cooling bath was removed and stirring was continued at room temperature for 3 hours. The reaction mixture was then poured into ice (150 mL), and the resulting mixture was extracted with diethyl ether (2×75 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide an oil. After addition of a seed crystal, the product was obtained as a solid. Yield: 1.99 g, 7.45 mmol, 83%. 1H NMR (400 MHz, CDCl3) δ 7.45 (br dd, J=10, 9 Hz, 1H), 8.46 (br ddd, J=9.1, 3, 3 Hz, 1H), 8.72 (dd, J=5.8, 2.7 Hz, 1H).

1. temperaturewas cooled in an ice bath
2. customthe cooling bath was removed
3. waitwas continued at room temperature for 3 hours
4. additionThe reaction mixture was then poured into ice (150 mL)
5. extractionthe resulting mixture was extracted with diethyl ether (2×75 mL)
6. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto provide an oil
11. additionAfter addition of a seed crystal
12. customthe product was obtained as a solid

ORD record

ord-763ba57086534057bf19c1668026aade

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697673B2