Ammonium Chloride → 7-Fluoro-1H-indole

Participants

Reaction Conditions

Reaction Steps

2 Fluoronitrobenzene (20.0 g, 0.142 mol) was dissolved in dry tetrahydrofuran (400 ml) and cooled to -50° C. Vinylmagnesium chloride (288 ml, 15% wt/vol) was added at -45° C. and stirred at this temperature for one hour. Poured onto saturated ammonium chloride (600 ml). Separated and aqueous extracted with diethyl ether (2×200 ml). Dried (MgSO4), filtered and concentrated in vacuo to yield a dark oil which was purified by column chromatography on silica using toluene as mobile phase. Fractions concentrated to yield a crystalline solid.

Provenance & Evidence