Iodine → HCID 84220500, compound

Temperature

-65 °C

To a solution of 2,5-dichloropyridine (95 g, 0.64 mol) in 1 L of dry ether was added dropwise t-BuLi (1.3 M, 500 mL, 0.65 mol) at −65° C. After addition, the mixture was stirred at −65° C. for 2 hrs, then the mixture was poured into a solution of iodine (180 g, 0.71 mol) in dry ether (700 mL) cooled at −60° C. Then the mixture was stirred at −65° C. for 1 hour and warmed to room temperature for another 1 hour. The mixture was quenched with H2O (400 mL), then extracted with EtOAc (200 mL). The organic phase was washed with sat. Na2SO3 (250 mL×3), sat. NaCl and dried over Na2SO4. Concentrated and the residue was purified via silica gel column (petroleum ether) to give title compound (57 g, ˜77% purity, 25% yield) as a light yellow solid, which was used directly in the next step.

1. additionAfter addition
2. temperaturecooled at −60° C
3. stirringThen the mixture was stirred at −65° C. for 1 hour
4. temperaturewarmed to room temperature for another 1 hour
5. customThe mixture was quenched with H2O (400 mL)
6. extractionextracted with EtOAc (200 mL)
7. washThe organic phase was washed with sat. Na2SO3 (250 mL×3), sat. NaCl
8. dry with materialdried over Na2SO4
9. concentrationConcentrated
10. customthe residue was purified via silica gel column (petroleum ether)

ORD record

ord-7e28f63d7f2a4fb8845d80b21f57ddcf

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056865B2