Reaktion #560918

Reaktionsgleichung

iodine

lithium diisopropylamide

2,6-difluoropyridine

→

2,6-difluoro-3-iodopyridine

Lösungsmittel

THF

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added via syringe
2. 2
   Waschenwashed with 10% aqueous sodium sulfite
3. 3
   SonstigeThe organic layer was separated
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe resulting crude product was purified by silica gel chromatography

Vorschrift

To a stirred solution of lithium diisopropylamide (4.34 mL, 8.69 mmol, 2.0 M solution in heptane/THF/ethylbenzene) in THF (20 mL) at −78° C. under a nitrogen atmosphere was added 2,6-difluoropyridine (0.79 mL, 8.69 mmol). The mixture was stirred at −78° C. for 45 min before iodine (2.21 g, 8.69 mmol) in THF (10 mL) was added via syringe. The reaction was stirred for an additional 30 min at −78° C. The reaction mixture was diluted with EtOAc and washed with 10% aqueous sodium sulfite. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography to give 2,6-difluoro-3-iodopyridine.

Quelle