Reaktion #333254

Reaktionsgleichung

6-fluoro-1H-indazole

potassium hydroxide

iodine

→

6-fluoro-3-iodo-1H-indazole

Ausbeute 81.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe maroon reaction mixture
2. 2
   Sonstigethen quenched with 10% aqueous Na2S2O3
3. 3
   workup.ADDITIONdiluted with water
4. 4
   ExtraktionThe mixture was extracted with EtOAc (2×)
5. 5
   WaschenThe combined organics were washed with water
6. 6
   Trocknendried over MgSO4
7. 7
   Einengenconcentrated

Vorschrift

To a solution of 6-fluoro-1H-indazole (5.50 g, 40.4 mmol) in DMF (150 ml) at room temperature was added potassium hydroxide (6.8 g, 121 mmol) and iodine (15.4 g, 60.6 mmol). The maroon reaction mixture was stirred at room temperature for 8 h then quenched with 10% aqueous Na2S2O3 and diluted with water. The mixture was extracted with EtOAc (2×). The combined organics were washed with water, sat LiCl, and sat NaCl, then dried over MgSO4 and concentrated to afford 8.6 g (81%) of 6-fluoro-3-iodo-1H-indazole as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.48 (dd, J=8.9, 5.1 Hz, 1H), 7.20 (dd, J=8.9, 2.1 Hz, 1H), 7.02 (td, J=9.1, 2.1 Hz, 1H)

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