Reaktion #43546

Reaktionsgleichung

water

5-Fluoro-1H-indole-2,3-dione

sodium hydride

p-methoxybenzyl chloride

→

5-Fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione

Ausbeute 80.0%

Lösungsmittel

DMF

DMF

ethyl acetate hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe solution was then stirred ca 2 hours
2. 2
   Extraktionfollowed by extraction into ethyl acetate
3. 3
   WaschenThe organic layer was washed twice with water
4. 4
   Trocknendried over MgSO4

Vorschrift

5-Fluoro-1H-indole-2,3-dione (956 mg, 5.79 mmol, 1 eq) was added as a solution in dry DMF to a stirred slurry of sodium hydride (278 mg, 11.6 mmol, 2 eq) in dry DMF drop wise over 15 minutes under an inert atmosphere with adequate pressure release to accommodate H2 evolution. The resulting mixture was stirred for 1 hour and p-methoxybenzyl chloride was added via syringe to the reaction. The solution was then stirred ca 2 hours and worked up by addition of water followed by extraction into ethyl acetate. The organic layer was washed twice with water and then dried over MgSO4. Column chromatography with ethyl acetate/hexane afforded 5-Fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione as a red solid (1.3 g, 80% yield). 1H NMR (CDCl3) δ (ppm): 7.3-7.24 (m, 3H), 7.20 (td, J=8.7, 2.7 Hz, 1H), 6.9-6.86 (m, 2H), 6.76 (dd, J=8.6, 3.6 Hz, 1H), 3.81 (s, 2H), 3.78 (s, 3H). LC/MS=286.1 (M+1).

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