Pyridine → HCID 57522524, compound

Temperature

0 °C

To a flame-dried round-bottomed flask was added 1,2-dihydroxy-4,5-diiodobenzene (1 equiv., 7.85 mmol, 2.84 g), CH2Cl2 (55 mL), and pyridine (5 equiv., 39 mmol, 3.10 g, 3.16 mL). The solution was cooled to 0° C. and Tf2O (2.2 equiv., 17.3 mmol, 4.88 g, 2.91 mL) was added dropwise via syringe over 10 min. The reaction was stirred for 6 h while warming to ambient temperature, then cooled to 0° C. and quenched with H2O (30 mL). The separated aqueous layer was extracted with CH2Cl2 (2×30 mL). The combined organic layers were dried with MgSO4 and filtered through a tall pad of silica. The pad was washed carefully with CH2Cl2 to avoid the elution of impurities, and the filtrate was concentrated in vacuo to afford 4,5-diiodo-1,2-phenylene bis(trifluoromethanesulfonate) (4.90 g, 7.82 mmol, quantitative) as an off-white solid. The product is optionally purified by column chromatography (10% EtOAc/Hex). TLC Rf=0.60 (10% EtOAc/Hex); Melting point 46.5-47.7° C.; 1H NMR (400 MHz): δ 7.91 (s, 2H); 13C NMR (100 MHz): δ 139.6, 133.4, 118.5 (q, JC,F=321.0 Hz), 108.0. FTIR: 1429, 1335, 1215, 1125, 1105, 868, 788, 745, 689 cm−1. HRMS-ESI: calc. for C8H2F6I2NaO6S2 (M+Na)+: 648.7184. found: 648.7164.

1. temperaturewhile warming to ambient temperature
2. temperaturecooled to 0° C.
3. customquenched with H2O (30 mL)
4. extractionThe separated aqueous layer was extracted with CH2Cl2 (2×30 mL)
5. dry with materialThe combined organic layers were dried with MgSO4
6. filtrationfiltered through a tall pad of silica
7. washThe pad was washed carefully with CH2Cl2
8. washthe elution of impurities
9. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-6ecc5f0a04f54713a1cd514bb7635f2e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079835B2