Iodine → 2,5-Dichloro-4-iodopyridine

Temperature

-78 °C

To a solution of LDA (11 mL of a 2 M in heptane/THF/ethylbenzene, 22 mmol) in THF (30 mL) at −78° C. was added a solution 2,5-dichloropyridine (3.3 g, 22 mmol) in THF (20 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1 h, and a solution of iodine (5.6 g, 22 mmol) in THF (20 mL) was added. The reaction mixture was stirred for 15 min, quenched with water, and warmed to rt. The reaction mixture was diluted with EtOAc, washed with water (1×), saturated Na2S2O3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. The crude reaction mixture was dissolved in dichloromethane (˜50 mL), diluted with hexanes (˜100 mL), and concentrated to a volume of ˜100 mL. The solid was collected by filtration, and washed with hexanes to give 2,5-dichloro-4-iodopyridine.

1. stirringThe reaction mixture was stirred for 15 min
2. customquenched with water
3. temperaturewarmed to rt
4. additionThe reaction mixture was diluted with EtOAc
5. washwashed with water (1×), saturated Na2S2O3 (1×), brine (1×)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude reaction mixture
10. concentrationconcentrated to a volume of ˜100 mL
11. filtrationThe solid was collected by filtration
12. washwashed with hexanes

ORD record

ord-6e66378c2f714dc79d7f0ebd3fc6c6ad

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791147B2